Methylamine → 6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

HRID 985282Notes

Reaction equation

HRID 985282 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:13]([OH:15])=O)=[CH:8][N:9]2[CH3:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:22][NH2:23]>>[CH3:22][NH:23][C:13]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH3:12])[CH:8]=1)=[O:15]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 221434786-methoxy-1-methyl-1H-indole-3-carboxylic acid

Product 1

HCID 221434906-methoxy-N,1-dimethyl-1H-indole-3-carboxamideYield 45%

Procedure

This material was prepared from 6-methoxy-1-methyl-1H-indole-3-carboxylic acid 16b (2.39 g, 10.9 mmole), oxalyl chloride and methylamine in a manner as previously described for example 16d to give a brown solid (1.08 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ7.97 (1H, d, J=8.7 Hz), 7.76 (2H, m), 6.99 (1H, d, J=2.3 Hz), 6.77 (1H, dd, J=2.3, 8.7 Hz), 3.80 (3H, s), 3.76 (3H, s), 2.74 (3H, s); ESIMS (MH+): 219.05.

Sources & evidence

ORD record
ord-6e5551098154428f90397930473a8527
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…