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. 2011 Sep 9;76(21):8781–8793. doi: 10.1021/jo201511d

Table 2. Indolation of Boc-THIQ 1h.

graphic file with name jo-2011-01511d_0007.jpg

        yield of indolation (%)
 deprotection
entry R X/Y product Fea Cub entry product yield (%)e
1 H CH/CH 3h 54 79 13 5h 100c
                89d
2 1-CH3 CH/CH 3i 65 70 14 5i 100c
                97d
3 2-CH3 CH/CH 3j 23 67 15 5j 100c
4 5-NH2 CH/C 3k 16 nc 16   np
5 5-OCH3 CH/C 3l 43 52 17 5l 99c
6 5-NO2 CH/C 3m 66 59 18 5m 100c
7 5-COOMe CH/C 3n 5 50 19   np
8 5-Cl CH/C 3o 72 66 20 5o 100c
9 6-Cl CH/CH 3p 56 75 21 5p 86c
10 7-NO2 C/CH 3q 70 46 22 5q 99c
11 H N/CH 3r 42 44 23 5r 100c
12 6-Cl N/N 3s nc 40 24   np
a

Fe(NO3)3·9H2O.

b

Cu(NO3)2·3H2O.

c

Conditions: TMSCl, MeOH, room temperature.

d

Conditions: ethylene glycol, 250 °C, microwave, 30 s.

e

yYield after deprotection of the Boc PG; np = not performed.