Dimethylformamide → Ethyl N-[1-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-(2-thienylsulfonyl)aminoacetate
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]1[S:23][CH:24]=[CH:25][N:26]=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[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]1[S:23][CH:24]=[CH:25][N:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-[1-(methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide (0.68 g), ethyl bromoacetate (0.23 mL), potassium carbonate (0.35 g) and N,N-dimethylformamide (6 mL) was stirred at room temperature for 4 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 obtained residue was subjected to silica gel column chromatography and the title compound (0.82 g, quantitative) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 124-125° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-edcadfc0aff54ec1a41bdbd500bc43c4
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957070B2
Reaction notes
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