Water → (3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one

HRID 537931Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:14])([CH3:13])[O:11]/[C:10](=[C:15]3/[C:16](=[O:25])[NH:17][C:18]4[C:23]/3=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)/[CH:9]=2)=[CH:4][CH:3]=1.[CH:26]([B-](F)(F)F)=[CH2:27].[K+].C(N(CC)CC)C.O>C(O)(C)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][C:12]1([CH3:14])[O:11]/[C:10](=[C:15]2/[C:16](=[O:25])[NH:17][C:18]3[C:23]/2=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)/[CH:9]=[C:8]1[C:5]1[CH:6]=[N:7][C:2]([CH:26]=[CH2:27])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 76 °C

Procedure

A mixture of 3-[4-(6-chloro-pyridin-3-yl)-5,5-dimethyl-5H-furan-(2E)-ylidene]-6-fluoro-1.3-dihydro-indol-2-one (60 mg, 0.17 mmol), potassium vinyltrifluoroborate (40 mg, 0.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with CH2Cl2, 10 mg, 0.012 mmol) and triethylamine (60 mg, 0.59 mmol) in isopropanol/water (10 mL/5 mL) solution was heated at 76° C. under nitrogen for 2.5 hours. The reaction was cooled to room temperature and poured into 100 mL of water. The resulting precipitates were filtered, washed with water and dried in vacuo to give (3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one as a brown solid. Yield: 50 mg, 85%.

Workup

temperatureThe reaction was cooled to room temperature
customThe resulting precipitates
filtrationwere filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-04ed3fc4ea71409d95c3e9701e6b1054
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865682B2

Reaction notes

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