Dichloromethane → 6-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid Butylamide
Reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=2)[N:10]([CH3:19])[C:9]=1[CH3:20])=[O:7])[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C(Cl)Cl>>[CH2:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[N:10]([CH3:19])[C:9]=1[CH3:20])=[O:7])[CH2:2][CH2:3][CH3:4]Participants
4
Procedure
This material was prepared by the reaction of 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid butylamide 62a (0.78 g, 2.84 mmole) with 1.0 M BBr3 in CH2Cl2 (8.53 ml, 8.53 mmole) in a manner as previously described for example 1d to give an off-white solid (0.623 g, 96%). 1H NMR (300 MHz, CD3OD) δ7.40 (1H, d, J=8.5 Hz), 6.64 (1H, d, J=2.1 Hz), 6.59 (1H, dd, J=2.1, 8.5 Hz), 3.50 (3H, s), 3.29 (2H, m), 2.48 (3H, s), 1.54 (2H, m), 1.36 (2H, m), 0.90 (3H, t, J=7.3 Hz); ESIMS (MH+): 261.15.
Sources & evidence
- ORD record
- ord-7434d424dca74e579486087b61073e47
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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