Water → HCID 57901750, compound

HRID 1851621Notes

Reaction equation

HRID 1851621 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[S:8]([N:11]([CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[CH:17]2)(=[O:10])=[O:9])=[O:2].[CH3:27][Mg]Br.O>O1CCCC1>[OH:2][CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[S:8]([N:11]([CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[CH:17]2)(=[O:10])=[O:9])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 57901766HCID 57901766, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57901750HCID 57901750, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-formyl-N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-3-sulfonamide (790 mg) in tetrahydrofuran (20 mL) was added methylmagnesium bromide (3.0 M, 1.5 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (272 mg, yield 33%) as white crystals. melting point 193° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e35fdbe54b7478c8308ed735db3e26b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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