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

HRID 14416

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-0dbb83c791174a899436c4d40bf3aa58
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732442B2

Linked notes

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