Thionyl Chloride → N-(Cyclopropylmethyl)-6-methoxy-1,2-dimethyl-1H-indole-3-carboxamide

HRID 1825129Notes

Reaction equation

HRID 1825129 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:14]([OH:16])=O)=[C:8]([CH3:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.O=S(Cl)Cl.[CH:21]1([CH2:24][NH2:25])[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][NH:25][C:14]([C:7]2[C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]([CH3:12])[C:8]=2[CH3:13])=[O:16])[CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 75646CyclopropanemethanamineHCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 22143562N-(Cyclopropylmethyl)-6-methoxy-1,2-dimethyl-1H-indole-3-carboxamideYield 38.4%

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid 16c (0.80, 3.65 mmole) with SOCl2 (0.799 ml, 10.95 mmole) and cyclopropylmethylamine (0.38 ml, 4.38 mmole) in a manner as previously described for example 9d to give a pale yellow solid (0.382 g, 38%). 1H NMR (300 MHz, CD3OD) δ 7.50 (1H, d, J=8.7 Hz), 6.81 (1H, d, J=2.2 Hz), 6.69 (1H, dd, J=2.2, 8.7 Hz), 3.74 (3H, s), 3.56 (3H, s), 3.20 (2H, m), 2.50 (3H, m), 1.07 (1H, m), 0.44 (2H, m}, 0.21 (2H, m); ESIMS (MH+): 273.10.

Sources & evidence

ORD record
ord-f35121e12abd4d92a5252a15e62a010e
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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