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Imidazole → tert-butyl (1-(4-(8-(1H-imidazol-1-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

HRID 1037415
ノート
印刷プレビュー

反応式

HRID 1037415 の反応式
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12.[NH:37]1[CH:41]=[CH:40][N:39]=[CH:38]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu](I)I>[N:37]1([C:2]2[N:3]=[CH:4][CH:5]=[C:6]3[C:11](=[O:12])[C:10]([C:13]4[CH:14]=[CH:15][C:16]([C:19]5([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:22][CH2:21][CH2:20]5)=[CH:17][CH:18]=4)=[C:9]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:8][C:7]=23)[CH:41]=[CH:40][N:39]=[CH:38]1
参加物反応条件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 795ImidazoleHCID 10796Cesium carbonateHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

生成物 1

HCID 86671059tert-butyl (1-(4-(8-(1H-imidazol-1-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate収率 32.5%

試薬・触媒・溶媒 2

HCID 83717
Copper iodide
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

tert-Butyl (1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate (63 mg, 0.115 mmol), imidazole (11 mg, 0.161 mmol), cesium carbonate (75 mg, 0.23 mmol) and copper (II) iodide (5 mg, 0.023 mmol) were dissolved in DMF (1 mL) in a microwave vial. The vial was sealed, evacuated and flushed twice with nitrogen. The reaction mixture was heated conventionally at 120° C. for 72 h. After cooling to RT, the resultant mixture was diluted with EtOAc, washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, 1:1 ethyl acetate/hexane) to give the title compound (20 mg, 24%). LCMS (Method I): RT=5.89 min, [M+H]+=535.

後処理

  1. customThe vial was sealed
  2. customevacuated
  3. customflushed twice with nitrogen
  4. temperatureAfter cooling to RT
  5. additionthe resultant mixture was diluted with EtOAc
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2a240891743d460790235ccbf6d7658a
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546376B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート