Water → 3-(Phenylethynyl)-5-(trifluoromethyl)pyridin-2-amine

HRID 14416

反応式

HRID 14416 の反応式
Br[C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[CH:14].O>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](Br)Br>[C:15]1([C:13]#[C:14][C:2]2[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 3

HCID 962WaterHCID 10821PhenylacetyleneHCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amine

生成物 1

HCID 231227943-(Phenylethynyl)-5-(trifluoromethyl)pyridin-2-amine

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
60 °C

実験手順

Under an atmosphere of argon, to a solution of 3-bromo-5-(trifluoromethyl)pyridin-2-amine (the compound described in Bio. Org. Med. Chem., 9, 1715 (1999)) (163 mg) in triethylamine (1.5 mL), ethynylbenzene (82 μL), bis(triphenylphosphine)palladium dichloride (43 mg) and copper bromide (14 mg) were added. The reaction mixture was stirred for overnight at 60° C. To the reaction mixture, water was added and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give the title compound (26 mg) having the following physical data.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-0dbb83c791174a899436c4d40bf3aa58
出典データセット
uspto-grants-2010_06
特許番号
US07732442B2

関連ノート

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