2-Thiopheneboronic acid → 3-Thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1Br)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:17]1[S:16][CH:20]=[CH:19][CH:18]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
3
Procedure
3-Thiophene-2-yl-1H-indole-2-carboxylic acid ethyl ester was prepared from 3-bromo-1H-indolecarboxylic acid ethyl ester and 2-thiopheneboronic acid followed the procedure of Example 11 Step 2 as a light yellow powder: 1H NMR (DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 4.30 (q, J=7.2 Hz, 2H), 7.12-7.16 (m, 1H), 7.17-7.20 (m, 1H), 7.31-7.34 (m, 1H), 7.36(dd, J=5.1, 1.5 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.63 (d, J=6.3 Hz, 1H), 7.71 (d, J=8.2 Hz, 1H), 12.02 (br s, 1H); MS (ESI) m/z 272 (MH+); 270 ([M−H]−).
Sources & evidence
- ORD record
- ord-8144f3e51f3544ae878d4932e286ccb4
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268159B2
Reaction notes
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