2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 66799599, compound

HRID 2172727Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:9]=2)[N:5]=[C:4]([C:22]([NH2:24])=[O:23])[CH:3]=1.[CH:25](B1OC(C)(C)C(C)(C)O1)=[CH2:26].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:10]2[CH:9]=[C:8]([C:6]3[N:5]=[C:4]([C:22]([NH2:24])=[O:23])[CH:3]=[C:2]([CH:25]=[CH2:26])[CH:7]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:16][CH:17]=1

Participants

Reactant 3

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HCID 11078149TBAF tetrahydrofuran

HCID 66799693HCID 66799693, compound

Product 1

HCID 66799599HCID 66799599, compoundYield 50%

Conditions

Temperature: 120 °C

Procedure

A 5 ml sealed microwave tube was charged with 4-chloro-6-[3-(4-fluoro-phenoxy)-phenyl]-pyridine-2-carboxylic acid amide (0.267 g, 0.78 mmol), vinyl boronic acid pinacol ester (0.180 g, 1.17 mmol, Aldrich) in three equivalents of TBAF/THF. The mixture was heated to 120° C. by microwave for 45 minutes. The mixture was chromatographed without workup by combiflash using a 40-gram silica column with a gradient of methanol (30% max) in chloroform to provide 0.130 g of 6-[3-(4-fluoro-phenoxy)-phenyl]-4-vinyl-pyridine-2-carboxylic acid amide as a clear oil in good purity (50% yield).

Workup

customA 5 ml sealed microwave tube
customThe mixture was chromatographed without workup by combiflash

Sources & evidence

ORD record: ord-58238858a8fe45d3b513cf9e7ac978d5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056832B2

Reaction notes

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