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 383505노트

반응식

HRID 383505 반응식
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

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 589262043-[4-(6-Chloro-pyridin-3-yl)-5,5-dimethyl-5h-furan-(2e)-ylidene]-6-fluoro-1,3-dihydro-indol-2-one

생성물 1

HCID 58926294(3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 21889133Propan-2-ol--water (1/1)용매

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온도
76 °C

실험 절차

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%.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-23c4a6ffcdf04342b63ef1c7d8ee6e6c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367664B2

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