Water → 1-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione

HRID 2385089노트

반응식

HRID 2385089 반응식
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10](I)=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:26].[Na+].[OH2:31]>C(#N)C.C(OCC)(=O)C.O.[Ru](Cl)(Cl)Cl>[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10](=[O:31])[C:9]2=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 23667635Sodium periodateHCID 673571561-(Diphenylmethyl)-3-iodo-4-fluoroindole

생성물 1

HCID 685968111-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione수율 25%

시약·촉매·용매 3

HCID 6093376Ruthenium trichloride hydrate촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(diphenylmethyl)-3-iodo-4-fluoroindole (8.85 g, 20.7 mmol) in a mixture of acetonitrile (25 mL) and water (5 mL) was added ruthenium (III) chloride monohydrate (0.30 g, 1.45 mmol) and sodium periodate (13.3 g, 62.2 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×25 mL), saturated aqueous ammonium chloride (3×25 mL) and brine (3×25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from acetonitrile to afford 1-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione (1.73 g, 25%) as an orange solid: mp 168-171° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.49-7.41 (m, 1H), 7.38-7.28 (m, 10H), 6.86 (dd, J=8.8, 8.8 Hz, 1H), 6.80 (s, 1H), 6.45 (d, J=8.1 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 178.3, 157.8, 157.7 (d, 1JC-F=261.0 Hz), 150.6 (d, 3JC-F=6.0 Hz), 139.7 (d, 2JC-F=10.0 Hz), 137.0, 128.5, 128.3, 127.8, 110.7 (d, 2JC-F=19.5 Hz), 108.8 (d, 4JC-F=2.9 Hz), 106.4 (d, 3JC-F=18.2 Hz), 28.7; MS (ES+) m/z 332.2 (M+23).

후처리

  1. washwashed with water (3×25 mL), saturated aqueous ammonium chloride (3×25 mL) and brine (3×25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-0fc35d7957e94cdda6826c73440f3acc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263606B2

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