Diisobutylaluminum hydride → 4-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

HRID 1177559ノート

反応式

HRID 1177559 の反応式
CC(C[AlH]CC(C)C)C.[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([C:32]#N)=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(C(C(C([O-])=O)O)O)([O-])=[O:37]>C(Cl)Cl>[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([CH:32]=[O:37])=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 671129224-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile

生成物 1

HCID 866387254-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

DIBAL-H (1.0M in hexanes) (185 μl, 0.185 mmol) was added to a solution of 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile (59.6 mg, 0.169 mmol) in DCM (2.7 mL) at 25° C., and the resulting solution was stirred at 25° C. for 45 min. Sat. aq. Na/K tartrate solution (3.0 mL) was added, and the resulting mixture was vigorously stirred for 15 min, then partitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes) provided 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde as a light yellow solid. MS (ESI) m/z: Calculated: 356.1; Observed: 357.1 (M++1).

後処理

  1. stirringthe resulting mixture was vigorously stirred for 15 min
  2. custompartitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-e038ce7cd8904649962cfcd546d09d44
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

読み込み中…