Pyridine → Methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoate

HRID 590058Notes

Reaction equation

HRID 590058 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=1[S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[Cl:12][C:3]1[C:2]([NH:1][S:27]([C:21]2[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:20]=2[F:19])(=[O:29])=[O:28])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 15132848Methyl 3-amino-2-chlorobenzoate

Product 1

HCID 57989637Methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoateYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure analogous to Intermediate 5, Step A using methyl 3-amino-2-chlorobenzoate (39 g, 211 mmol) in DCM (200 mL) was added pyridine (51 g, 633 mmol) and 2,6-difluorobenzene-1-sulfonyl chloride (49.1 g, 232 mmol) the title compound was obtained (62 g, 81.6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (dd, J=1.8 Hz, 8.38 Hz, 1H), 7.72-7.79 (br, 1H), 7.56 (dd, J=1.8 Hz, 7.94 Hz, 1H), 7.45-7.53 (m, 1H), 7.28 (dd, J=7.9 Hz, 8.4 Hz, 1H), 6.95-7.01 (m, 2H), 3.89 (s, 3H).

Sources & evidence

ORD record
ord-fcb161f8ab5f46648ef6f324f91ccfb2
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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