Chlorosuccinimide → 2-chloro-6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

HRID 1825165Notes

Reaction equation

HRID 1825165 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:21]([NH:23][CH3:24])=[O:22])=[CH:16][N:17]2[CH3:20])=[CH:13][CH:12]=1>C(Cl)(Cl)(Cl)Cl.CN(C=O)C>[CH3:24][NH:23][C:21]([C:15]1[C:14]2[C:18](=[CH:19][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[N:17]([CH3:20])[C:16]=1[Cl:1])=[O:22]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 221434906-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 221435532-chloro-6-methoxy-N,1-dimethyl-1H-indole-3-carboxamideYield 87%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-Chlorosuccinimide (0.150 g, 1.12 mmole) was added to a solution of 6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide 75a (0.243 g, 1.11 mmole) in CCl4 (10 ml) and DMF (3 ml). The reaction mixture was heated to 60° C. for 3 h and concentrated. The residue was purified by reverse phase chromatography eluting with 0–1% CH3OH in 1:1 EtOAc and CH2Cl2 to give a brown colored oil (0.243 g, 87% yield); 1H NMR (300 MHz, CDCl3) δ 7.61 (1H, d, J=8.6 Hz), 6.38 (1H, d, J=8.6 Hz), 6.19 (1H, s), 3.35 (3H, s), 2.96 (3H, s), 2.52 (3H, s); ESIMS (MH+): 253.05.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase chromatography
  3. washeluting with 0–1% CH3OH in 1:1 EtOAc and CH2Cl2

Sources & evidence

ORD record
ord-2fd37caf68314770abef278bbe717582
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

Loading…