Water → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-methanesulfonyl-1H-indole-2-carboxylic acid

HRID 1071681

Reaction equation

HRID 1071681 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[O:4].[H-].[Na+].Br[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=1)=[O:23].O>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:22]([CH2:21][N:6]2[C:7]3[C:12](=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=3)[CH:13]=[C:5]2[C:3]([OH:2])=[O:4])=[O:23])=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 735868Methyl 5-(methylsulfonyl)-1H-indole-2-carboxylateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamide

Product 1

HCID 223943401-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-methanesulfonyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g 5-Methanesulfonyl-1H-indole-2-carboxylic acid methyl ester in 10 ml DMF, 158 mg (60% in oil) sodium hydride were added at RT. After stirring for 10 min 985 mg 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added and the mixture was stirred for 2 h. After the addition of 7 ml water the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate and concentrated under reduced pressure. The residue was taken-up in 10 ml water/THF 1:2 and treated with 2 ml aqueous KOH solution (10%). After stirring for 16 h at RT the reaction mixture was acidified with hydrochloric acid (5M). The precipitate was collected by filtration and dried in vacuo to yield the product as a yellow solid. Yield: 1.1 g.

Workup

  1. additionwere added
  2. filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. additiontreated with 2 ml aqueous KOH solution (10%)
  5. stirringAfter stirring for 16 h at RT the reaction mixture
  6. filtrationThe precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-69649a9a966e4eac82c451d1023afcf9
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Linked notes

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