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

HRID 1666473Notes

Reaction equation

[F: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>[F: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-fluoro-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (585 mg, 0.001 mol) in dry CH2Cl2 (7 mL) cooled to 0° C. was added trifluoroacetic acid (0.99 mL, 0.012 mol). The reaction mixture was stirred for 30 min at 0° C. and then for 1 h at RT. 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 (469 mg, 100%). 1H NMR (500 MHz, CDCl3): δ 9.82 (m, 1H), 8.43 (s, 1H), 7.95 (d, J=8 Hz, 1H), 7.07 (d, J=9 Hz, 1H), 6.83 (q, J=13.5 Hz, 2H), 6.43 (s, 1H), 3.29 (s, 1H), 3.17 (s, 1H), 2.85 (m, 1H), 2.72 (s, 1H).

Workup

waitfor 1 h at RT
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-17961cbca92c4b4d9c93df434e84396b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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