Dimethylformamide → ethyl 7-amino-4-chloro-1-(methoxymethyl)-1H-indole-2-carboxylate

HRID 1851399Notes

Reaction equation

HRID 1851399 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][O:12][CH3:13])[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2.[Cl:19]N1C(=O)CCC1=O.CN(C)C=O>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]2[C:10]=1[N:9]([CH2:11][O:12][CH3:13])[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 57475944ethyl 7-amino-1-(methoxymethyl)-1H-indole-2-carboxylate

Product 1

HCID 57476018ethyl 7-amino-4-chloro-1-(methoxymethyl)-1H-indole-2-carboxylateYield 25.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 7-amino-1-(methoxymethyl)-1H-indole-2-carboxylate (3.18 g), N-chlorosuccinimide (1.74 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. 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 and the title compound (0.91 g, yield 25%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

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-72afceb34bec43698432d74f754ad214
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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