tert-Butyl 4-oxopiperidine-1-carboxylate → 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 1806200ノート

反応式

HRID 1806200 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.O=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C[O-].[Na+]>CO>[NH2:13][C:11]([C:9]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[C:5]2[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]=1)=[O:12]

参加物

5

反応物 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 10942334Sodium MethoxideHCID 596006575-bromo-1H-indole-7-carboxamide

生成物 1

HCID 596006561,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate収率 514.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 5-bromo-1H-indole-7-carboxamide (10 g, 41.84 mmol) in methanol (5 mL), 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (684 mg, 3.42 mmol) and sodium methoxide (0.5 M in THF, 13.7 mL, 6.84 mmol) were added. The reaction mixture was stirred at reflux temperature for 16 hours. All solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The combined organic phase was dried over MgSO4 and concentrated under reduced pressure, and purified by flash column chromatography (ethyl acetate/hexanes, 1/1) to give the desired product (7.4 g, 43%).

後処理

  1. temperatureat reflux temperature for 16 hours
  2. customAll solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. dry with materialThe combined organic phase was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash column chromatography (ethyl acetate/hexanes, 1/1)

出典と根拠

ORDレコード
ord-c70a59257e6c46828ef63950411f96dd
出典データセット
uspto-grants-2013_01
特許番号
US08354406B2

反応ノート

読み込み中…