Potassium Phosphate, Tribasic → HCID 67315543、化合物

HRID 1011895ノート

反応式

HRID 1011895 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=2)[CH:9]=1)=[O:4].[O:18]1[C:22](B(O)O)=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC(O)=O.CC(O)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:22]2[O:18][C:19]3[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=3[CH:21]=2)[CH:9]=1)=[O:4]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2776266Benzo[b]furan-2-boronic acidHCID 13370531HCID 13370531、化合物

生成物 1

HCID 67315543HCID 67315543、化合物収率 58.3%

試薬・触媒・溶媒 3

HCID 4144353Palladium (II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

1.40 g (4.74 mmol) of 5-(3-bromo-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (6′) (and ethyl ester) was dissolved in 15 ml of toluene and 1.6 ml of H2O. Then 1.54 g (9.49 mmol) of benzo[b]furan-2-boronic acid, 5.42 g (25.52 mmol) of K3PO4, 0.29 g (1.04 mmol) of tricyclohexylphosphine and 0.117 g (0.52 mmol) of palladium-II-acetate were added. The reaction mixture was degassed (argon) several times at each addition. The reaction was heated (100° C.) for 24 h. At RT, the mixture was partitioned between chilled water/EtOAc (3×). The organic phases were washed with water, with aqueous sat. NaHCO3, dried (Na2SO4), filtered (black palladium complex stayed with Na2SO4) and evaporated. Then the residual product was dissolved in hot CH2Cl2 and crystallized at RT. It was filtered to give 0.918 g (58%) of 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as white powder. MS: 332.2 (M+).

後処理

  1. customThe reaction mixture was degassed (argon) several times
  2. additionat each addition
  3. customAt RT, the mixture was partitioned
  4. temperaturebetween chilled water/EtOAc (3×)
  5. washThe organic phases were washed with water, with aqueous sat. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered (black palladium complex stayed with Na2SO4)
  8. customevaporated
  9. dissolutionThen the residual product was dissolved in hot CH2Cl2
  10. customcrystallized at RT
  11. filtrationIt was filtered

出典と根拠

ORDレコード
ord-3b03feb1f7244efd9c2ef1b08aa255d7
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

反応ノート

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