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

HRID 1798378노트

반응식

HRID 1798378 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
135 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-2d639a93871d4cf684454838b5440a50
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343953B2

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