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

HRID 924738ノート

反応式

HRID 924738 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
135 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-b3b7b2ed26194d21a8769b12e3852890
出典データセット
uspto-grants-2016_03
特許番号
US09283226B2

反応ノート

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