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

HRID 1670952Notes

Reaction equation

HRID 1670952 reaction equation
ClC1N=C(/C=C(/C2C=C(N[S:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])C=CC=2)\O)C=CN=1.[NH2:29][C:30]1[C:31]([Cl:40])=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34].N1C=CC=CC=1.FC1C=CC=C(F)C=1S(Cl)(=O)=O>C(Cl)Cl>[Cl:40][C:31]1[C:30]([NH:29][S:18]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])(=[O:20])=[O:19])=[CH:39][CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 15132848Methyl 3-amino-2-chlorobenzoateHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

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-d7d4127c19d540c8a352deefd89daf98
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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