Sodium Carbonate → HCID 86680380, 화합물

HRID 83553노트

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HRID 83553 반응식
[Cl: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>[Cl: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 71287834HCID 71287834, 화합물HCID 86680350HCID 86680350, 화합물

생성물 1

HCID 86680380HCID 86680380, 화합물수율 78%

시약·촉매·용매 3

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

실험 절차

Under argon atmosphere, to 2-[3-chloro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (269 mg) were sequentially added a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (181 mg) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (2.0 ml), a 2M aqueous solution of sodium carbonate (1.0 ml), tricyclohexylphosphine (36 mg) and palladium (II) acetate (15 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 subjected to elution with ethyl acetate. The filtrate was extracted with ethyl acetate. The resulting 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: n-hexane/ethyl acetate=3/7) to give the titled compound (196 mg).

후처리

  1. customprepared
  2. filtrationthe mixture was filtered through Celite
  3. washsubjected to elution with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe resulting 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: n-hexane/ethyl acetate=3/7)

출처 및 근거

ORD 기록
ord-ee0f15b2c23e4dae85b670896d594d15
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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