Sodium Carbonate → 1-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine

HRID 83491ノート

反応式

HRID 83491 の反応式
I[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([NH2:13])[CH:3]=1.[F:14][C:15]([F:27])([F:26])[O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=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:7]1([N:6]2[C:2]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([O:16][C:15]([F:14])([F:26])[F:27])[CH:18]=3)=[CH:3][C:4]([NH2:13])=[N:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 86680350HCID 86680350、化合物

生成物 1

HCID 712877301-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine収率 44%

試薬・触媒・溶媒 2

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

実験手順

To a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (605 mg) in ethylene glycol dimethyl ether (12 ml) were sequentially added 3-(trifluoromethoxy)phenyl boronic acid (481 mg), a 2M aqueous solution of sodium carbonate (6 ml), tricyclohexylphosphine (119 mg), palladium acetate (48 mg), and the mixture was stirred for 2 hours at reflux. This reaction mixture was cooled to room temperature, and a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and then the mixture was filtered through Celite. 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 concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (298 mg).

後処理

  1. temperatureat reflux
  2. filtrationthe mixture was filtered through Celite
  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=2/1)

出典と根拠

ORDレコード
ord-8b8b806c94904a039738a8eb683df116
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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