Sodium Carbonate → HCID 86680366、化合物

HRID 83531ノート

反応式

HRID 83531 の反応式
[F: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>[F: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

参加物

9

反応物 5

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 71287745HCID 71287745、化合物HCID 86680350HCID 86680350、化合物

生成物 1

HCID 86680366HCID 86680366、化合物収率 77.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 2-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (49 mg) were sequentially added a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (36 mg) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (1.0 ml), a 2M aqueous solution of sodium carbonate (0.5 ml), tricyclohexylphosphine (7.3 mg) and palladium (II) acetate (3.0 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 extracted with ethyl acetate. The filtrate was extracted with ethyl acetate, the separated 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: chloroform/methanol=9/1) to give the titled compound (37 mg).

後処理

  1. customprepared
  2. filtrationthe mixture was filtered through Celite
  3. extractionextracted with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe separated 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: chloroform/methanol=9/1)

出典と根拠

ORDレコード
ord-296bbfb0c1874b98b73aa9ab915231e7
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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