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 383505ノート

反応式

HRID 383505 の反応式
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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

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

反応条件

温度
76 °C

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-23c4a6ffcdf04342b63ef1c7d8ee6e6c
出典データセット
uspto-grants-2013_02
特許番号
US08367664B2

反応ノート

読み込み中…