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

HRID 1961762Notes

Reaction equation

HRID 1961762 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-c0134729dec64248b5fa80f50f8b60c6
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

Loading…