2-Chloropyridine-3-sulfonyl chloride → ethyl 7-{[(2-chloropyridin-3-yl)sulfonyl]amino}-4-methyl-1H-indole-2-carboxylate

HRID 1994773Notes

Reaction equation

HRID 1994773 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[Cl:17][C:18]1[C:23]([S:24](Cl)(=[O:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1>N1C=CC=CC=1>[Cl:17][C:18]1[C:23]([S:24]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]3[C:10]=2[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]3)(=[O:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 102199682-Chloropyridine-3-sulfonyl chlorideHCID 57476149ethyl 7-amino-4-methyl-1H-indole-2-carboxylate

Product 1

HCID 86619904ethyl 7-{[(2-chloropyridin-3-yl)sulfonyl]amino}-4-methyl-1H-indole-2-carboxylateYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 7-amino-4-methyl-1H-indole-2-carboxylate (1.00 g) in pyridine (10 mL) was added 2-chloropyridine-3-sulfonyl chloride (1.99 g) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with 10% aqueous citric acid solution and saturated brine, dried (MgSO4), and concentrated to give ethyl 7-{[(2-chloropyridin-3-yl)sulfonyl]amino}-4-methyl-1H-indole-2-carboxylate (1.32 g) as a crude oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed successively with 10% aqueous citric acid solution and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3db20d08648c4cc5bcf9f5eb6fa28209
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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