Potassium Phosphate, Tribasic → HCID 67315543, 화합물

HRID 1011895노트

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HRID 1011895 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 67315543HCID 67315543, 화합물수율 58.3%

시약·촉매·용매 3

HCID 4144353Palladium (II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3b03feb1f7244efd9c2ef1b08aa255d7
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

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