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Methanol → (2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

HRID 2375109
ノート
印刷プレビュー

反応式

HRID 2375109 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[CH2:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.CO>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH2:17][CH3:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 887MethanolHCID 6228DimethylformamideHCID 136141708(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 135984714(2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester収率 69%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 8857Ethyl Acetate溶媒

実験手順

Palladium (10% on activated carbon) (0.23 g, 0.198 mmol) was added to a solution of the title compound of Example 164 (0.65 g, 1.99 mmol) in 1:10 N,N-dimethylformamide:methanol (11 mL). The reaction mixture was purged with H2 and stirred at room temperature under H2 (1 atm.) for 5 hours. The palladium was filtered and the volatile components were removed in vacuo. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 1.2:1 dichloromethane:ethyl acetate to afford the title compound (0.45 g, 1.37 mmol) as a yellow solid in 69% yield.

後処理

  1. customThe reaction mixture was purged with H2
  2. filtrationThe palladium was filtered
  3. customthe volatile components were removed in vacuo
  4. dissolutionThe resulting residue was dissolved in methanol
  5. washeluted with 1.2:1 dichloromethane

出典と根拠

ORDレコード
ord-2203b3a66b064123b3cfb86b0cc69a27
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07462713B2

反応ノート

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