Potassium Phosphate, Tribasic → 3-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole

HRID 406594ノート

反応式

HRID 406594 の反応式
[Br:1][C:2]1[CH:6]=[C:5](Br)[N:4]([CH3:8])[N:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:6]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=2[Cl:9])[N:4]([CH3:8])[N:3]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 177502292-Chloro-4-fluorobenzeneboronic acidHCID 666141313,5-dibromo-1-methyl-1H-pyrazole2 回

生成物 1

HCID 666135773-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3,5-dibromo-1-methyl-1H-pyrazole (i.e. the product of Step B) (2.00 g, 8.33 mmol) in toluene (40 mL) was sparged with a stream of argon for 45 minutes, and then 2-chloro-4-fluorophenylboronic acid (1.59 g, 9.11 mmol), potassium phosphate tribasic (5.30 g, 25.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.41 mmol) were added. The reaction mixture was heated at 90° C. for 3 h, and then cooled to room temperature and diluted with ethyl acetate (250 mL). The mixture was washed with water (25 mL) and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a white solid (620 mg).

後処理

  1. customwas sparged with a stream of argon for 45 minutes
  2. temperaturecooled to room temperature
  3. washThe mixture was washed with water (25 mL) and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material was purified by silica gel chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant)

出典と根拠

ORDレコード
ord-8624a151838f4200b05e2ca0b859e5e5
出典データセット
uspto-grants-2014_06
特許番号
US08754115B2

反応ノート

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