Dimethylformamide → 1-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

HRID 1159843Notes

Reaction equation

HRID 1159843 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.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[F:28]>>[Cl:21][C:22]1[CH:23]=[C:24]([S:29]([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:30])=[O:31])[CH:25]=[CH:26][C:27]=1[F:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595135471-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamineYield 14.4%

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 3-chloro-4-fluorobenzene-1-sulfonyl chloride (25 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 white solid. MS (ESI+) for C18H18ClFN2O3S m/z 397 (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-52ec87b012444beba3a53b3996b07081
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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