7-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one → 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365057ノート

反応式

HRID 1365057 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1

参加物

4

反応物 2

HCID 129470247-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 577324247-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine収率 52.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A round-bottomed flask was charged with 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (500 mg) and tetrahydrofuran (20 mL). To this mixture was added lithium aluminum hydride (1.8 mL of 1M solution in tetrahydrofuran). The reaction was stirred overnight at room temperature, then quenched with water and 10% sodium hydroxide. The quenched mixture was filtered through Celite and the filter was washed with ethyl acetate. The filtrate was dried over magnesium sulfate, filtered and concentrated to an oil. Silica gel purification provided 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg) as a yellow powder. H1 NMR (d6-dmso): 7.43-7.50 (m, 1H), 7.40 (dt, 1H), 7.18-7.28 (m, 3H), 6.75-6.81 (m, 2H), 6.71 (d, 1H), 3.95 (m, 2H), 3.49 (m, 2H). Mass (ES+)=319.1 (100%).

後処理

  1. customquenched with water and 10% sodium hydroxide
  2. filtrationThe quenched mixture was filtered through Celite
  3. washthe filter was washed with ethyl acetate
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customSilica gel purification

出典と根拠

ORDレコード
ord-1de3bd6af1a74c39a5c20a8966452836
出典データセット
uspto-grants-2011_02
特許番号
US07888503B2

反応ノート

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