Potassium Phosphate, Tribasic → N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2,6-difluorobenzamide

HRID 1036109Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[N:6][CH:7]=1.[F:19][C:20]1([F:39])[O:24][C:23]2[CH:25]=[C:26]([CH3:38])[C:27](B3OC(C)(C)C(C)(C)O3)=[CH:28][C:22]=2[O:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(#N)C.O>[F:39][C:20]1([F:19])[O:24][C:23]2[CH:25]=[C:26]([CH3:38])[C:27]([C:2]3[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]4[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=4[F:17])=[N:6][CH:7]=3)=[CH:28][C:22]=2[O:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

Palladium tetrakis-triphenylphosphine (23 mg, 20 μmol) was added to a degassed solution of bromide 17 (129 mg, 0.4 mmol) and boronate 14 (117 mg, 0.4 mmol) in dioxane:acetonitrile:water (9:9:2, 2.0 mL) and potassium phosphate (125 mg, 0.6 mmol). The resulting mixture was heated under argon at 80° C. with stirring for 1.5 hours. The mixture was then cooled, extracted with dichloromethane (3×7 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-30% ethyl acetate in hexane) provided 10 (124 g, 78%) as a crystalline solid: LRESIMS m/z 406.1 [M+H]+, calcd. for C19H12F4N3O3 406.1.

Workup

temperatureThe mixture was then cooled
extractionextracted with dichloromethane (3×7 mL)
dry with materialdried with sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2711de18e0dc49c2bd6ee895227bb4d4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546403B2

Reaction notes

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