Dimethylformamide → HCID 59513546, compound

HRID 1159840Notes

Reaction equation

HRID 1159840 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.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[S:31](Cl)(=[O:33])=[O:32])[CH:24]=[CH:23][CH:22]=1>>[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:31]([C:29]1[CH:28]=[CH:27][CH:26]=[C:25]3[C:30]=1[N:21]=[CH:22][CH:23]=[CH:24]3)(=[O:32])=[O:33])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 292208-Quinolinesulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513546HCID 59513546, compoundYield 11%

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 8-quinolinesulfonyl 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 (3 mg, 11%) as a white solid. MS (ESI+) for C21H21N3O3S m/z 396 (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-943aab17f6ac46c1b97bf035900b6c12
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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