Pyridine → Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate

HRID 1670938Notes

Reaction equation

HRID 1670938 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].N1C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[S:28]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 18412404Ethyl 3-amino-4-fluorobenzoate

Product 1

HCID 57989990Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

Workup

  1. waitAfter 16 h
  2. concentrationthe reaction mixture was concentrated
  3. customtriturated with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7bb22567301b484ca32d285ae22367f0
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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