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

HRID 239236Notes

Reaction equation

HRID 239236 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)[CH3:2].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[S:21](Cl)(=[O:23])=[O:22].N1C=CC=CC=1>C(Cl)Cl>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[S:21]([NH:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11400Ethyl 3-aminobenzoateHCID 27342712,6-Difluorobenzenesulfonyl chloride

Product 1

HCID 8823788Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}benzoateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl-3-aminobenzoate (50 mL, 333 mmol) and 2,6-difluorobenzenesulfonyl chloride (44.2 mL, 333 mmol) in DCM (300 mL) at 0° C. was added pyridine (32.2 mL, 400 mmol). The reaction mixture was warmed to rt, stirred for 36 h, and quenched with 2 mL NH3 (7 M in MeOH). The suspension washed with 10% NaHSO4 and the organic extracts combined and passed through a short column of silica gel. Residual material was flushed from the column with 10% MeOH/EtOAc. The organic extracts were combined and the solvent removed under reduced pressure to provide 107.9 g (95%) of the title compound of Step A. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.20 (s, 1H), 7.77 (s, 1H), 7.71 (t, J=7.4 Hz, 1H), 7.63 (d, J=7.3 Hz, 1H), 7.35-7.49 (m, 2H), 7.29 (t, J=9.3 Hz, 2H), 4.28 (q, J=7.1 Hz, 2H), and 1.29 (t, J=7.1 Hz, 3H).

Workup

  1. customquenched with 2 mL NH3 (7 M in MeOH)
  2. washThe suspension washed with 10% NaHSO4
  3. customResidual material was flushed from the column with 10% MeOH/EtOAc
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d3e07a52a775468dad001055eee21ad0
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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