2-Chloro-4-methylpyrimidine → N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

HRID 1670953Notes

Reaction equation

HRID 1670953 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](/[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)\[OH:10])[CH:5]=[CH:4][N:3]=1.[Cl:29]C1C(NS(C2C(F)=CC=CC=2F)(=O)=O)=CC=CC=1C(OC)=O.ClC1N=C(C)C=CN=1>>[Cl:29][C:12]1[C:11](/[C:9](/[OH:10])=[CH:8]\[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:16][CH:15]=[CH:14][C:13]=1[NH:17][S:18]([C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[F:28])(=[O:19])=[O:20]

Participants

4

Reactant 3

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989637Methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoateHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 136342910N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamideYield 73.5%

Procedure

Following a procedure analogous to Intermediate 5, Step B using methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoate (31 g, 85.9 mmol) and 2-chloro-4-methylpyrimidine (12.2 g, 94.5 mmol) the title compound was obtained (33 g, 73.5% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.47-13.52 (br, 0.96H), 8.50-8.56 (m, 0.13H), 8.38 (d, J=5.3 Hz, 1H), 7.78-7.82 (m, 0.15H), 7.62-7.73 (m, 2H), 7.40-7.50 (m, 1.18H), 7.17-7.30 (m, 1.77H), 6.90-6.97 (m, 2.29H), 6.83 (d, J=5.3 Hz, 1H), 5.65 (s, 1H), 4.28 (s, 0.26H). MS (ES+): 458 [M+H]+.

Sources & evidence

ORD record
ord-4658a0504cc54c39b43b3217b4f3c9a7
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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