Cesium carbonate → Ethyl 4-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]butanoate

HRID 423330ノート

反応式

HRID 423330 の反応式
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:22]=4)[C:20]#[N:21])[O:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:20]([C:19]1[CH:22]=[C:15]([C:13]2[O:12][N:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH:3]=[CH:2][N:1]4[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:14]=2)[CH:16]=[CH:17][C:18]=1[O:23][CH:24]([CH3:26])[CH3:25])#[N:21]

参加物

5

反応物 3

HCID 10796Cesium carbonate2 回HCID 76300Ethyl 4-bromobutyrate5 回HCID 593183965-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

生成物 1

HCID 59318367Ethyl 4-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]butanoate収率 41.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile (D49) (100 mg, 0.29 mmol), ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and cesium carbonate (189 mg, 0.58 mmol) in DMF (2 ml) was heated at 80° C. for 1 hour. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated overnight at 80° C. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and cesium carbonate (189 mg, 0.58 mmol) and heated for 24 hours. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated for 24 hours. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated for 6 hours. Added EtOAc (20 ml) and washed with water (20 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ethanol to give the title compound (55 mg) as a white solid. MS (ES) C26H26N4O4 requires 458; found 459 (MH+).

後処理

  1. washAdded EtOAc (20 ml) and washed with water (20 ml)
  2. dry with materialDried over MgSO4
  3. customevaporated off the solvent
  4. customThe residue was crystallised from ethanol

出典と根拠

ORDレコード
ord-81c615eea6f249df9dcd2bdcb5ad99db
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

反応ノート

読み込み中…