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

HRID 2271412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271412
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

Komponenten

6

Edukt 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

Produkt 1

HCID 90461250(R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehydeAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8e722e4bf2ec4ca885d167e2c19fd7ff
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120757B2

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