Trifluoroacetic acid → 2-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

HRID 1666461Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:21]=1)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:21]=[C:20]([CH:19]=[C:4]([CH:5]=[C:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH:3]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (1.2 g, 2.33 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (1.79 mL, 23.37 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and at RT for 1 h. The reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2 three times. The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound (1.15 g, 100%). 1H NMR (500 MHz, CDCl3): δ 8.43 (s, 1H), 7.93 (d, J=6.75 Hz, 1H), 7.23 (s, 1H), 7.20 (s, 1H), 7.05 (d, J=8.45 Hz, 1H), 6.89 (s, 1H), 6.39 (s, 1H), 3.23 (m, 2H), 3.12 (m, 2H), 2.75 (m, 2H), 2.64 (m, 2H); m/z (413.2, 415.2, M+ H+).

Workup

customThe reaction mixture was quenched with saturated aqueous NaHCO3
extractionextracted with CH2Cl2 three times
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-5d8f341b7faf492db596d403003d8fa6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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