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

HRID 83541ノート

反応式

HRID 83541 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](I)=[CH:11][C:10]([NH2:14])=[N:9]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.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:18]2[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]=2)=[CH:11][C:10]([NH2:14])=[N:9]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 75806TricyclohexylphosphineHCID 71287745HCID 71287745、化合物HCID 866803721-(2-Fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine

生成物 1

HCID 866803741-(2-Fluorophenyl)-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 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

To a solution of 1-(2-fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine (38 mg) in 1,4-dioxane (0.4 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 (52 mg) prepared according to the same procedures as Preparation 15, palladium (II) acetate (3 mg), tricyclohexylphosphine (7 mg), 2M aqueous solution of potassium carbonate (0.2 ml) at room temperature, and the mixture was stirred at 105° C. for 4 hours. After removing the aqueous layer of this reaction mixture, the organic layer was filtered through silica gel (5 g), and subjected to elution with ethyl acetate. The filtrate was concentrated under reduced pressure, and 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. customAfter removing the aqueous layer of this reaction mixture
  3. filtrationthe organic layer was filtered through silica gel (5 g)
  4. washsubjected to elution with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. 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-58b730552709451e872d74d35a7cb538
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

読み込み中…