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

HRID 1407508ノート

反応式

HRID 1407508 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6093376Ruthenium trichloride hydrate触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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, 3J=18.2 Hz), 28.7; MS (ES+) m/z 332.2 (M+23).

後処理

  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

出典と根拠

ORDレコード
ord-cb95618a361642ddbb77ee8181817f89
出典データセット
uspto-grants-2014_12
特許番号
US08916580B2

反応ノート

読み込み中…