Table 1.
Screening study for the development of flow catalytic Suzuki-Miyaura cross-coupling of 5-iodo-2’-deoxyuridine with 3-methoxyphenyl boronic acid
| ||||||||
|---|---|---|---|---|---|---|---|---|
| Sr.No | 1a | 2a 1.6 eq |
SerrKap palladacycle Mole % |
Solvent H2O:EtOH |
Flow Rate (Residence time) |
Pressure (kPa) |
Base 1.3 eq |
% Yield |
| 1) |
176 mg (0.167 M) |
120 mg (0.263 M) |
0.5 | 4 + 2 mL |
0.7 mL/min (25 min) |
9–10 | 138 mg | 20 |
| 2) |
176 mg (0.167 M) |
120 mg (0.263 M) |
1 | 4 + 2 mL |
0.7 mL/min (25 min) |
9–10 | 138 mg | 35 |
| 3) |
176 mg (0.125 M) |
120 mg (0.197 M) |
1 | 5 + 3 mL |
0.7 mL/min (25 min) |
9–10 | 138 mg | 45 |
| 4) |
176 mg (0.083 M) |
120 mg (0.132 M) |
1 | 8 + 4 mL |
0.7 mL/min (25 min) |
9–10 | 138 mg | 65 |
| 5) |
176 mg (0.083 M) |
120 mg (0.132 M) |
1 | 8 + 4 mL |
1.0 mL/min (17.5 min) |
15–16 | 138 mg | 52 |
| 6) |
176 mg (0.067 M) |
120 mg (0.105 M) |
1 | 10 + 5 mL |
1.0 mL/min (17.5 min) |
15–16 | 138 mg | 86 |
| 7) |
176 mg (0.067 M) |
120 mg (0.105 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 83 |
| 8) |
176 mg (0.067 M) |
120 mg (0.105 M) |
0.75 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 62 |
| 9) |
176 mg (0.067 M) |
120 mg (0.105 M) |
0.5 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 46 |
| 10) |
176 mg (0.067 M) |
120 mg (0.105 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 |
90 μl (NEt3) |
56 |
| 11) |
176 mg (0.067 M) |
120 mg (0.105 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 |
97 μl (DBU) |
65 |
| 12) |
176 mg (0.067 M) |
120 mg (0.105 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 |
90 mg (K2CO3) |
41 |
| 13) |
176 mg (0.067 M) |
114 mg (1.5 eq.) (0.1 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 83 |
| 14) |
176 mg (0.067 M) |
106 mg (1.4 eq.) (0.093 M) |
1 | 10 + 5 ml |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 83 |
| 15) |
176 mg (0.067 M) |
98 mg (1.3 eq.) (0.086 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 | 138 mg | 83 |
| 16) |
176 mg (0.067 M) |
90 mg (1.2 eq.) (0.079 M) |
1 | 10 + 5 mL |
2.0 mL/min (8.0 min 45 sec) |
35–36 | 138 mg | 71 |
| 17) |
176 mg (0.067 M) |
98 mg (1.3 eq.) (0.086 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 |
127 mg (1.2) |
89 |
| 18) |
176 mg (0.067 M) |
98 mg (1.3 eq.) (0.086 M) |
1 | 10 + 5 mL |
2.0 mL/min (8 min 45 sec) |
35–36 |
111 mg (1.05) |
95 |