Sodium Carbonate → 1-(4-Chlorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine

HRID 83536노트

반응식

HRID 83536 반응식
[Cl: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.[F:15][C:16]1[CH:17]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:19]=[C:20]([CH2:22][O:23][C@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:18]3[CH:19]=[C:20]([CH2:22][O:23][C@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])[CH:21]=[C:16]([F:15])[CH:17]=3)=[CH:11][C:10]([NH2:14])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 71287745HCID 71287745, 화합물HCID 866803681-(4-Chlorophenyl)-5-iodo-1H-pyrazol-3-ylamine

생성물 1

HCID 866803701-(4-Chlorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine

시약·촉매·용매 2

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

실험 절차

Under argon atmosphere, to a solution of 1-(4-chlorophenyl)-5-iodo-1H-pyrazol-3-ylamine (35 mg) in 1,2-dimethoxyethane (0.7 ml) were sequentially added 2-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (46 mg) prepared according to the same procedures as Preparation 15, a 2M aqueous solution of sodium carbonate (0.35 ml), tricyclohexylphosphine (6.1 mg) and palladium (II) acetate (2.5 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, was subjected to elution with ethyl acetate. The filtrate was 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=1/1) to give the titled compound.

후처리

  1. customprepared
  2. customaccording to the same procedures as Preparation 15
  3. filtrationfiltered through Celite
  4. washwas subjected to elution with ethyl acetate
  5. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: n-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-6251f1e5c6c3401cbae93e80c1014e48
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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