Potassium Phosphate, Tribasic → (R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehyde

HRID 2271412ノート

反応式

HRID 2271412 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH:10]=2)O1.I[C:23]1[C:24]([CH:34]=[O:35])=[N:25][N:26]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:18]1[CH2:17][CH2:16][N:15]([CH:12]2[CH2:13][CH2:14][C:9]([C:23]3[C:24]([CH:34]=[O:35])=[N:25][N:26]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[CH:27]=3)=[CH:10][CH2:11]2)[CH2:20][CH2:19]1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 592386904-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)morpholineHCID 904606424-iodo-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde

生成物 1

HCID 90461250(R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehyde収率 81.1%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)morpholine (293 mg, 1.00 mmol, 1.00 equiv), (R/S) 4-iodo-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde (306 mg, 1.00 mmol, 1.00 equiv), K3PO4 (640 mg, 3.02 mmol, 3.02 equiv) and Pd(dppf)Cl2 (65.1 mg, 0.10 mmol, 0.10 equiv) in ethylene glycol dimethyl ether (5 mL) was stirred under nitrogen at 85° C. for 12 h. The reaction was cooled to room temperature and concentrated under vacuum. The residue was purified on a silica gel column eluted with 50-100% of ethyl acetate in petroleum ether to give 280 mg (81%) of (R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehyde as a brown oil. LCMS (method C, ESI): RT=0.70 min, m/z=346.2 [M+H]+.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified on a silica gel column
  4. washeluted with 50-100% of ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-8e722e4bf2ec4ca885d167e2c19fd7ff
出典データセット
uspto-grants-2015_09
特許番号
US09120757B2

反応ノート

読み込み中…