Sodium Carbonate → 1-(4-Fluorophenyl)-5-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1H-pyrazol-3-ylamine

HRID 83568노트

반응식

HRID 83568 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](I)=[CH:11][C:10]([NH2:14])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[CH:24]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:27]3[CH:28]=[CH:23][CH:24]=[C:25]([CH2:29][O:30][CH2:31][C:32]([F:33])([F:34])[F:35])[CH:26]=3)=[CH:11][C:10]([NH2:14])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 71287843HCID 71287843, 화합물HCID 86680375HCID 86680375, 화합물

생성물 1

HCID 712877501-(4-Fluorophenyl)-5-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1H-pyrazol-3-ylamine수율 51%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Under argon atmosphere, to a solution of 1-(4-fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine (70 mg) prepared in Preparation 18 in 1,2-dimethoxyethane (0.7 ml) were sequentially added 4,4,5,5-tetramethyl-2-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-[1,3,2]dioxaborolane (80 mg), a 2M aqueous solution of sodium carbonate (0.35 ml), tricyclohexylphosphine (13.0 mg) and palladium (II) acetate (5.2 mg) at room temperature, and the mixture was stirred at 100° C. for 2 hours. This reaction mixture was cooled to room temperature, 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 sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to give the titled compound (43 mg).

후처리

  1. filtrationfiltered through Celite
  2. washsubjected to elution with ethyl acetate
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-91d311e57b334d3aab7ee8511953fae3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

반응 노트

불러오는 중…