Trifluoroacetic acid → 7-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1407402ノート

反応式

HRID 1407402 の反応式
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:18]3[C:29]([OH:30])=[CH:28][C:21]4[N:22]([CH3:27])[C:23](=[O:26])[CH2:24][O:25][C:20]=4[CH:19]=3)(O)[C:9]2=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[C:32]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:18]3[C:29]([OH:30])=[CH:28][C:21]4[N:22]([CH3:27])[C:23](=[O:26])[CH2:24][O:25][C:20]=4[CH:19]=3)[C:9]2=[O:31])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 685977597-(1-benzhydryl-3-hydroxy-2-oxoindolin-3-yl)-6-hydroxy-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

生成物 1

HCID 686010007-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one収率 71%

実験手順

To a solution of 7-[1-(diphenylmethyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one (4.0 g, 8.1 mmol) in trifluoroacetic acid (1.8 mL, 24.4 mmol) was added triethylsilane (3.9 mL, 24.4 mmol) and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography with ethyl acetate in hexanes (10 to 100% gradient) to afford 7-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one (2.66 g, 71%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ9.53 (s, 1H), 7.44-7.28 (m, 10H), 6.99-6.95 (m, 3H), 6.89-6.84 (m, 2H), 6.54 (s, 1H), 6.40 (m, 1H), 4.90 (s, 1H), 4.57 (s, 2H), 3.21 (s, 3H); MS (ES+) m/z 477.0 (M+1).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by column chromatography with ethyl acetate in hexanes (10 to 100% gradient)

出典と根拠

ORDレコード
ord-a11f4f24fee14f34b404e256ee0098ab
出典データセット
uspto-grants-2014_12
特許番号
US08916580B2

反応ノート

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