Dimethylformamide → HCID 57475956, compound

HRID 1851413Notes

Reaction equation

HRID 1851413 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. The filtrate was concentrated, subjected to NH silica gel column chromatography, and eluted with an 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 an ethyl acetate-hexane mixture (2:1)

Sources & evidence

ORD record
ord-7061af09eca14ea3b641798b815f1521
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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