Dimethylformamide → HCID 57475956, compound

HRID 1960242Notes

Reaction equation

HRID 1960242 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:22]([NH2:24])=[O:23].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.[Cl-].[Na+].O>[CH:27]1([CH2:26][N:13]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[N:4]([CH2:3][O:2][CH3:1])[C:5]([C:22]([NH2:24])=[O:23])=[CH:6]3)[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 57475954HCID 57475954, compound

Product 1

HCID 57475956HCID 57475956, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.0 g), (bromomethyl)cyclopropane (456 mg), potassium carbonate (1.13 g) and N,N-dimethylformamide (5 ml) was stirred at 85° C. for 20 hr. The reaction mixture was diluted with ethyl acetate and saturated brine. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated. The residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate-hexane mixture (2:1) to give the title compound (820 mg, yield 72%) as an amorphous form.

Workup

  1. washThe organic layer was washed with aqueous sodium bicarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated
  5. washeluted with ethyl acetate-hexane mixture (2:1)

Sources & evidence

ORD record
ord-1ec6d4ed23e74ea9929846ec75510fd4
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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