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

HRID 83536ノート

反応式

HRID 83536 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6251f1e5c6c3401cbae93e80c1014e48
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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