Pyridine → 3,5-Dichloro-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamide

HRID 25495

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1.N1C=CC=CC=1>O>[Cl:28][C:26]1[CH:25]=[C:24]([S:29]([NH:18][C:16]2[CH:17]=[C:12]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=4)[CH:13]=[CH:14][C:15]=2[O:19][CH3:20])(=[O:30])=[O:31])[CH:23]=[C:22]([Cl:21])[CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with 3,5-dichlorobenzenesulfonyl chloride (0.256 g, 1.0 mmol) and pyridine (3 mL) was added, and the reaction mixture was heated briefly to 50° C. and then allowed to stand overnight at room temperature. Water (7 mL) was added and the mixture allowed to stand 2 hours at room temperature. The mixture was partitioned between water (200 mL) and ethyl acetate (200 mL), and the organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL), dried (magnesium sulfate), filtered, and concentrated to a purple-tinted solid. The solid was triturated with hexanes/ethyl acetate, 1/1, v/v to give the product (0.355 g), mp 217-219° C.

Workup

additionwas added
waitto stand 2 hours at room temperature
customThe mixture was partitioned between water (200 mL) and ethyl acetate (200 mL)
washthe organic layer was washed with 1N HCl (100 mL), water (100 mL), and brine (100 mL)
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated to a purple-tinted solid
customThe solid was triturated with hexanes/ethyl acetate, 1/1, v/v

Sources & evidence

ORD record: ord-f5d15fd5ce7c4bd0ab9fc741344a9428
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858739B2

Linked notes

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