Table 3.
Library Data for Compounds 14{1–121}
| product | 9 | R3 | method | yield (%)b | purity (%)e | product | 9 | R3 | method | yield (%)b | purity (%)e |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 14{1} | 9{1} | 10{5} | A | 39 | 84 | 14{65} | 9{8} | 6{10} | C | 77 | >99 |
| 14{2} | 9{2} | 10{9} | Aa | 47 | >99 | 14{66} | 9{12} | 6{9} | C | 76 | >99 |
| 14{3} | 9{3} | 10{1} | A | 51 | >99 | 14{67} | 9{13} | 6{5} | C | 82c | 99 |
| 14{4} | 9{3} | 10{6} | A | 38 | 99 | 14{68} | 9{13} | 6{9} | C | 67 | >99 |
| 14{5} | 9{3} | 10{7} | A | 55 | 99 | 14{69} | 9{17} | 6{6} | C | 52 | 98 |
| 14{6} | 9{5} | 10{1} | A | 88c | >99 | 14{70} | 9{18} | 6{2} | C | 85 | >99 |
| 14{7} | 9{5} | 10{6} | A | 78 | >99 | 14{71} | 9{19} | 6{1} | C | 78 | >99 |
| 14{8} | 9{5} | 10{7} | A | 83 | >99 | 14{72} | 9{19} | 6{7} | C | 57 | >99 |
| 14{9} | 9{8} | 10{10} | A | 71c | 99 | 14{73} | 9{19} | 6{9} | C | 78 | >99 |
| 14{10} | 9{9} | 10{1} | A | 57 | >99 | 14{74} | 9{19} | 6{12} | C | 34 | 99 |
| 14{11} | 9{10} | 10{10} | A | 73c | 98 | 14{75} | 9{21} | 6{5} | C | 83c | >99 |
| 14{12} | 9{11} | 10{1} | A | 62 | >99 | 14{76} | 9{21} | 6{7} | C | 61 | >99 |
| 14{13} | 9{11} | 10{6} | A | 53 | 99 | 14{77} | 9{21} | 6{9} | C | 86c | >99 |
| 14{14} | 9{14} | 10{1} | A | 47 | >99 | 14{78} | 9{1} | 12{1} | D | 66c | 96 |
| 14{15} | 9{14} | 10{2} | A | 28 | >99 | 14{79} | 9{1} | 12{3} | D | 61c | 99 |
| 14{16} | 9{14} | 10{6} | A | 51 | >99 | 14{80} | 9{3} | 12{1} | D | 47c | 95 |
| 14{17} | 9{14} | 10{7} | A | 69 | >99 | 14{81} | 9{3} | 12{2} | D | 72c | 98 |
| 14{18} | 9{14} | 10{9} | A | 53 | 99 | 14{82} | 9{3} | 12{3} | D | 58 | 97 |
| 14{19} | 9{15} | 10{3} | A | 32 | 98 | 14{83} | 9{5} | 12{1} | D | 69c | 99 |
| 14{20} | 9{17} | 10{1} | A | 72c | >99 | 14{84} | 9{5} | 12{3} | D | 71c | >99 |
| 14{21} | 9{17} | 10{6} | A | 67 | >99 | 14{85} | 9{6} | 12{1} | D | 76c | 98 |
| 14{22} | 9{17} | 10{7} | A | 73c | >99 | 14{86} | 9{9} | 12{3} | D | 71 | 99 |
| 14{23} | 9{17} | 10{9} | A | 85c | >99 | 14{87} | 9{11} | 12{2} | D | 71 | >99 |
| 14{24} | 9{18} | 10{9} | Aa | 69c | >99 | 14{88} | 9{12} | 12{1} | D | 78 | 99 |
| 14{25} | 9{19} | 10{1} | A | 81c | >99 | 14{89} | 9{13} | 12{1} | D | 69 | 93 |
| 14{26} | 9{19} | 10{6} | A | 73 | >99 | 14{90} | 9{14} | 12{1} | D | 61 | 98 |
| 14{27} | 9{21} | 10{1} | A | 83c | >99 | 14{91} | 9{14} | 12{4} | D | 57 | 98 |
| 14{28} | 9{21} | 10{6} | A | 71c | >99 | 14{92} | 9{17} | 12{1} | D | 76c | 99 |
| 14{29} | 9{22} | 10{1} | A | 67 | >99 | 14{93} | 9{17} | 12{4} | D | 68 | 96 |
| 14{30} | 9{23} | 10{3} | A | 57c | 98 | 14{94} | 9{19} | 12{2} | D | 58 | 99 |
| 14{31} | 9{23} | 10{9} | A | 68c | 99 | 14{95} | 9{19} | 12{3} | D | 64c | >99 |
| 14{32,(33)} | 9{5} | 10{4} | B | 34(29)c,d | >99 | 14{96} | 9{20} | 12{1} | D | 81c | >99 |
| 14{34,(35)} | 9{6} | 10{6} | B | 44(33)c,d | >99 | 14{97} | 9{21} | 12{3} | D | 53c | >99 |
| 14{36,(37)} | 9{7} | 10{1} | B | 46(27)c,d | >99 | 14{98} | 9{22} | 12{3} | D | 57 | >99 |
| 14{38,(39)} | 9{8} | 10{1} | B | 41(31)c,d | >99 | 14{99} | 9{1} | 13{1} | E | 58c | 98 |
| 14{40,(41)} | 9{8} | 10{6} | B | 43(35)c,d | >99 | 14{100} | 9{1} | 13{3} | E | 29 | >99 |
| 14{42,(43)} | 9{10} | 10{1} | B | 49(32)c,d | >99 | 14{101} | 9{1} | 13{5} | E | 56c | >99 |
| 14{44,(45)} | 9{20} | 10{6} | B | 37(28)c,d | >99 | 14{102} | 9{1} | 13{6} | E | 26 | >99 |
| 14{46} | 9{1} | 6{6} | C | 43 | 96 | 14{103} | 9{1} | 13{7} | E | 27 | 96 |
| 14{47} | 9{2} | 6{2} | C | 81c | 99 | 14{104} | 9{3} | 13{1} | E | 59 | 98 |
| 14{48} | 9{2} | 6{4} | C | 82c | 99 | 14{105} | 9{3} | 13{5} | E | 37 | 97 |
| 14{49} | 9{3} | 6{1} | C | 77c | >99 | 14{106} | 9{5} | 13{1} | E | 71c | 99 |
| 14{50} | 9{3} | 6{8} | C | 41 | 96 | 14{107} | 9{5} | 13{5} | E | 73 | >99 |
| 14{51} | 9{3} | 6{9} | C | 48 | 98 | 14{108} | 9{6} | 13{6} | E | 37 | >99 |
| 14{52} | 9{4} | 6{2} | C | 21 | 97 | 14{109} | 9{7} | 13{1} | E | 76c | >99 |
| 14{53} | 9{4} | 6{3} | C | 18 | 98 | 14{110} | 9{7} | 13{2} | E | 69c | >99 |
| 14{54} | 9{5} | 6{1} | C | 83 | >99 | 14{111} | 9{7} | 13{4} | E | 48 | >99 |
| 14{55} | 9{5} | 6{2} | C | 84 | >99 | 14{112} | 9{7} | 13{5} | E | 55 | >99 |
| 14{56} | 9{5} | 6{5} | C | 73 | 98 | 14{113} | 9{8} | 13{1} | E | 76c | >99 |
| 14{57} | 9{5} | 6{9} | C | 81 | 98 | 14{114} | 9{8} | 13{3} | E | 59 | >99 |
| 14{58} | 9{5} | 6{11} | C | 69 | >99 | 14{115} | 9{13} | 13{1} | E | 80c | 99 |
| 14{59} | 9{5} | 6{12} | C | 31 | 95 | 14{116} | 9{15} | 13{1} | E | 53 | >99 |
| 14{60} | 9{6} | 6{5} | C | 69 | >99 | 14{117} | 9{16} | 13{1} | E | 58 | 98 |
| 14{61} | 9{6} | 6{9} | C | 60 | >99 | 14{118} | 9{17} | 13{5} | E | 71c | >99 |
| 14{62} | 9{7} | 6{2} | C | 79c | 99 | 14{119} | 9{18} | 13{1} | E | 74c | >99 |
| 14{63} | 9{7} | 6{9} | C | 57 | >99 | 14{120} | 9{20} | 13{5} | E | 59 | >99 |
| 14{64} | 9{8} | 6{8} | C | 72 | >99 | 14{121} | 9{21} | 13{5} | E | 54c | 99 |
a
The THP ether-protected boronic acid 10{9} was deprotected in situ using aq. HCl in THF at room temperature.
b
Isolated yield after preparative HPLC.
c
Isolated yield after column chromatography.
d
The number in parentheses is the yield of Suzuki-Miyaura direct coupling product.
e
UV purity determined at 214 nm after preparative HPLC.