Ethyl Acetate → 9-(2-Bromoacetyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532942ノート

反応式

HRID 532942 の反応式
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][N:10]1[C:20](=[O:21])[CH2:19][NH:18][C:17](=[O:22])[CH:16]=[C:11]12)=[CH2:5])C.C1C(=O)N([Br:30])C(=O)C1.CCOC(C)=O>C1COCC1.O.[Cl-].[Na+].O>[Br:30][CH2:3][C:4]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][N:10]1[C:20](=[O:21])[CH2:19][NH:18][C:17](=[O:22])[CH:16]=[C:11]12)=[O:5]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 867113859-(1-Ethoxyvinyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

生成物 1

HCID 867113869-(2-Bromoacetyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione収率 62.7%

試薬・触媒・溶媒 2

HCID 21881883Oxolane--water (1/1)溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

111-2. A solution of 9-(1-ethoxyvinyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (1.2 g, 4.02 mmol) in a mixture of THF/H2O (3:1, 40 mL) was treated with NBS (716 mg, 4.02 mmol) and the mixture was stirred at 0° C. for 10 min. The mixture was partioned between AcOEt and brine and the org. phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (880 mg) that was used as it is in the next step. UPLC-MS: MS 349.0 (M+H+); UPLC rt 0.69 min.

後処理

  1. customphase was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4efcf9cc1a094d2cb568c4b24e4d16e8
出典データセット
uspto-grants-2014_10
特許番号
US08853203B2

反応ノート

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