Sodium Carbonate → 6-(3-Methyl-1-trityl-1H-pyrazol-4-yl)-nicotinonitrile

HRID 924738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924738
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH3:10][C:11]1[C:15](B(O)O)=[CH:14][N:13]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:10][C:11]1[C:15]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)=[CH:14][N:13]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:12]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 22031628(3-Methyl-1-trityl-1H-pyrazol-4-yl)boronic acid

Produkt 1

HCID 593319716-(3-Methyl-1-trityl-1H-pyrazol-4-yl)-nicotinonitrileAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a solution of 6-Chloro-nicotinonitrile (0.2 g, 1.49 mmol) and 3-methyl-1-trityl-1H-pyrazole-4-boronic acid* (0.5 g, 1.36 mmol) in ethylene glycol dimethyl ether (3 ml), was added sodium carbonate (0.36 g, 3.39 mmol) in water (1.5 ml). The reaction mixture was degassed with nitrogen before addition of tetrakis(triphenylphosphine)palladium (0) and then heated in a CEM microwave at 135° C. for 30 minutes (50 W power). Reaction partitioned between water and ethyl acetate, aqueous basified with 2N NaOH, organic extracts were combined, dried (MgSO4) and solvent removed. Crude product suspended in small volume of methanol, white precipitate filtered to afford the title compound (0.32 g, 53% yield). LC/MS: (PS-A2) Rt 4.52 [M+H]+ 427.26. * This starting material can be made by the method described in EP1382603A1

Aufarbeitung

  1. customThe reaction mixture was degassed with nitrogen before addition of tetrakis(triphenylphosphine)palladium (0)
  2. customReaction
  3. custompartitioned between water and ethyl acetate, aqueous basified with 2N NaOH, organic extracts
  4. dry with materialdried (MgSO4) and solvent
  5. customremoved
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-b3b7b2ed26194d21a8769b12e3852890
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283226B2

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