Sodium Carbonate → HCID 86680366, 화합물

HRID 83531노트

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HRID 83531 반응식
[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([CH2:8][O:9][C@H:10]([CH3:15])[C:11]([F:14])([F:13])[F:12])[CH:7]=1.I[C:26]1[N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:29]=[C:28]([NH2:37])[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])O.[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:26]2[N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:29]=[C:28]([NH2:37])[CH:27]=2)[CH:5]=[C:6]([CH2:8][O:9][C@H:10]([CH3:15])[C:11]([F:12])([F:13])[F:14])[CH:7]=1

참가 물질

9

반응물 5

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 71287745HCID 71287745, 화합물HCID 86680350HCID 86680350, 화합물

생성물 1

HCID 86680366HCID 86680366, 화합물수율 77.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To 2-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (49 mg) were sequentially added a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (36 mg) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (1.0 ml), a 2M aqueous solution of sodium carbonate (0.5 ml), tricyclohexylphosphine (7.3 mg) and palladium (II) acetate (3.0 mg) at room temperature, and the mixture was stirred at 100° C. for 2 hours. This reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added thereto, the mixture was filtered through Celite, and extracted with ethyl acetate. The filtrate was extracted with ethyl acetate, the separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1) to give the titled compound (37 mg).

후처리

  1. customprepared
  2. filtrationthe mixture was filtered through Celite
  3. extractionextracted with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1)

출처 및 근거

ORD 기록
ord-296bbfb0c1874b98b73aa9ab915231e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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