Potassium Carbonate → 4-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

HRID 1045186ノート

反応式

HRID 1045186 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH:7]=[O:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[N:4][N:5]([CH3:9])[C:6]=2[CH:7]=[O:8])=[CH:13][CH:12]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27946344-bromo-1-methyl-1H-pyrazole-5-carbaldehyde

生成物 1

HCID 866425044-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde (0.500 g), 4-chlorophenylboronic acid (0.455 g), tetrabutylammonium bromide (0.853 g), potassium carbonate (0.914 g) and palladium acetate (0.030 g) were stirred together in 5 mL of water and heated to 45° C. After stirring for 2.5 hours, the reaction was diluted with ethyl acetate (75 mL) and washed with water (25 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude material. The solid was chromatographed over silica gel (SF40-80) eluted using a gradient of 5% to 25% ethyl acetate/hexanes over 30 minutes.

後処理

  1. washwashed with water (25 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-53acc79a5fbd47a4a2b88e5eb3f16c49
出典データセット
uspto-grants-2013_10
特許番号
US08563735B2

反応ノート

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