4-(4-Iodobenzyl)pyridine → (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]acrylamide

HRID 1994151Notes

Reaction equation

I[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:18][C:17]=1[C:27]([F:30])([F:29])[F:28]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:26])/[CH:24]=[CH:25]/[C:2]2[CH:14]=[CH:13][C:5]([CH2:6][C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[CH:4][CH:3]=2)=[CH:18][C:17]=1[C:27]([F:28])([F:29])[F:30]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-(4-iodobenzyl)pyridine (129 mg, 0.44 mmol), TEA (67 μL, 0.48 mmol), Pd(PPh3)4 (254 mg, 0.222 mmol) and N-[4-chloro-3-(trifluoromethyl)-phenyl]acrylamide (0.120 g, 0.44 mmol) in DMF (4.4 mL) was heated at 95° C. for 3 h. The reaction mixture was cooled to rt, diluted with water, extracted with EtOAc, washed with brine, dried over NaSO4, filtered and concentrated. The residue was purified by column chromatography to give the title compound (161 mg, 40%). LCMS: (FA) ES+ 417.2 (M+1).

Workup

temperatureThe reaction mixture was cooled to rt
extractionextracted with EtOAc
washwashed with brine
dry with materialdried over NaSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-05a3a00f04e34fb0a218462cbe3ed1ad
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652041B2

Reaction notes

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