Acetonitrile → 6-(2-Phenylethynyl)-4-(trifluoromethyl)pyridin-2-amine

HRID 535384Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.C(N([CH2:18][CH3:19])CC)C.[C:20](#N)[CH3:21]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl.[Cu]I.C1COCC1>[C:21]1([C:18]#[C:19][C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=2)[CH:20]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-chloro-4-(trifluoromethyl)pyridin-2-amine (1.0 g, 5.09 mmol) ethynylbenzene (779 mg, 7.63 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (372 mg, 0.51 mmol), copper(I) iodide (96 mg, 0.51 mmol), triethylamine (1.8 ml, 12.7 mmol), ACN (10 ml) and THF (5 ml) is stirred for 6 h at 90° C. The mixture is concentrated in vacuo, water is added (100 ml) and the mixture extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 680 mg (51%). HPLC-MS: M+H=263.

Workup

concentrationThe mixture is concentrated in vacuo, water
additionis added (100 ml)
extractionthe mixture extracted with EtOAc
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customThe product is purified by NP chromatography

Sources & evidence

ORD record: ord-7b3f7c91b600460e8ded7a0cead3274b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

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