HCID 46318655, compound → HCID 57942367, compound

HRID 1438560Notes

Reaction equation

Br[C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[Br:32][C:33]1[CH:44]=[CH:43][CH:42]=[CH:41][C:34]=1[C:35](N(OC)C)=[O:36]>C1COCC1>[Br:32][C:33]1[CH:44]=[CH:43][CH:42]=[CH:41][C:34]=1[C:35]([C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:21])([F:22])[F:20])[CH:13]=2)(=[O:10])=[O:11])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1)=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (250 mg, 0.50 mmol) in 4.0 ml of THF under nitrogen atmosphere at 0° C. was added drop-wise 0.6 mLl (1.2 mmol) of isopropylmagnesium chloride. The mixture was then stirred for 20 min at 0° C. followed by addition of a solution of 2-Bromo-N-methoxy-N-methyl-benzamide(244 mg, 1.0 mmol) in 1mL of THF. The mixture was stirred at room temperature overnight, quenched with saturated ammonium chloride and extracted with ethyl acetate. After concentration of the solvent the residue was purified by flash chromatograph (20% ethyl acetate in hexane) to afford 180 mg of title compound as an off white solid. MS: (M+Na)/z=621.2, (M−32)/z=567.0.

Workup

stirringThe mixture was stirred at room temperature overnight
customquenched with saturated ammonium chloride
extractionextracted with ethyl acetate
customAfter concentration of the solvent the residue was purified by flash chromatograph (20% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-641a46a8312645f09c55efd87ac223ca
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622583B2

Reaction notes

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