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

HRID 2271412노트

반응식

HRID 2271412 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-8e722e4bf2ec4ca885d167e2c19fd7ff
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120757B2

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