2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 86710110, compound

HRID 1468295Notes

Reaction equation

[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[N:13]3[CH:14]=[C:15](I)[C:16]([C:18]#[N:19])=[CH:17][C:12]3=[N:11][C:10]=2[C:21]([F:24])([F:23])[F:22])[CH2:4][CH2:3]1.[CH3:26][C:27]1(C)C(C)(C)OB(C=C)O1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[N:13]3[CH:14]=[C:15]([CH:26]=[CH2:27])[C:16]([C:18]#[N:19])=[CH:17][C:12]3=[N:11][C:10]=2[C:21]([F:24])([F:23])[F:22])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(4,4-Difluorocyclohexylmethyl)-6-iodo-2-trifluoromethylimidazo[1,2-a]pyridine-7-carbonitrile (20.0 mg, 0.0430 mmol) obtained in step 2 was dissolved in 1,2-dichloromethane (0.60 mL), and the solution was stirred at 60° C. for 1 hour after adding 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (24.0 mg, 0.153 mmol), tetrakis(triphenylphosphine)palladium(0) (4.93 mg, 0.00426 mmol), and water (0.2 mL). The reaction mixture was filtered through Celite (registered trademark), and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→50/50) to give 3-(4,4-difluorocyclohexylmethyl)-2-trifluoromethyl-6-vinylimidazo[1,2-a]pyridine-7-carbonitrile (11.0 mg, yield 70%).

Workup

filtrationThe reaction mixture was filtered through Celite (registered trademark)
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→50/50)

Sources & evidence

ORD record: ord-c4cd555fe1364e89be0fb9566ff65646
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000186B2

Reaction notes

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