Dimethylformamide → 1-{1-[(1,2-Dimethyl-1H-imidazol-4-yl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

HRID 1159847Notes

Reaction equation

HRID 1159847 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CN(C=O)C.[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[C:23]1[CH3:31]>>[CH3:21][N:22]1[CH:26]=[C:25]([S:27]([N:8]2[C:9]3[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)(=[O:29])=[O:28])[N:24]=[C:23]1[CH3:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27362561,2-Dimethylimidazole-4-sulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595135511-{1-[(1,2-Dimethyl-1H-imidazol-4-yl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamineYield 15.8%

Procedure

To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride (21 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at rt over night. The reaction was quenched by addition of water. Purification by preparative HPLC/UV (System B) afforded the title product (4 mg, 14%) as a brown solid. MS (ESI+) for C17H22N4O3S m/z 386 (M+H)+.

Workup

  1. stirringto stir at rt over night
  2. customThe reaction was quenched by addition of water
  3. customPurification by preparative HPLC/UV (System B)

Sources & evidence

ORD record
ord-62793de840d9479eb4753b359ceecc7c
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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