Oxalyl chloride → 6-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid cyclopropylamide

HRID 985208Notes

Reaction equation

HRID 985208 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:13]([OH:15])=O)=[C:3]1[CH3:16].C(Cl)(=O)C(Cl)=O.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>>[CH:23]1([NH:26][C:13]([C:4]2[C:5]3[C:10](=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]=2[CH3:16])=[O:15])[CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 207679146-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid cyclopropylamideYield 82%

Procedure

This material was prepared from 1,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid 16c (500 mg, 2.3 mmole), oxalyl chloride (0.4 ml, 4.6 mmole) and cyclopropylamine (1.6 ml, 23 mmole) in a manner as previously described for example 16d to give 480 mg (82%) of a white solid. 1H NMR (DMSO-d6 δ7.57 (1H, d, J=3.8 Hz), 7.50 (1H, d, J=8.8 Hz), 6.99 (1H, d, J=2.3 Hz), 6.71 (1H, dd, J=2.3, 8.8 Hz), 3.78 (3H, s), 3.63 (3H, s), 2.83-2.80 (1H, m), 2.51 (3H, s), 0.68-0.62 (2H, m), 0.57-0.53 (2H, m).

Sources & evidence

ORD record
ord-5e5050547159475bbf25c3c516eeb000
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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