Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate → Ethyl 1-(6-chloropyridin-2-yl)-5-(trifluoromethyl)-1H-1,2,3-triazole-4-carboxylate

HRID 1255228Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[N:5]=1)=[N+:2]=[N-:3].C(OC=[C:15]([C:21](=O)[C:22]([F:25])([F:24])[F:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C(#N)C>[Cl:10][C:6]1[N:5]=[C:4]([N:1]2[C:21]([C:22]([F:23])([F:25])[F:24])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:3]=[N:2]2)[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of the title compound from Example 330 Step A (300 mg, 1.94 mmol) in acetonitrile (4 mL) was added ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate (0.284 mL, 1.94 mmol) followed by TEA (0.271 mL, 1.94 mmol), and the mixture was heated at 70° C. After 16 h, the reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 65% EtOAc in hexanes) provided the title compound as a yellow oil: LCMS m/z 320.85 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.03 (t, J=7.9 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 4.55 (q, J=7.2 Hz, 2H), 1.49 (t, J=7.2 Hz, 3H).

Workup

concentrationthe reaction mixture was concentrated in vacuo
customPurification by flash chromatography on silica gel (0 to 65% EtOAc in hexanes)

Sources & evidence

ORD record: ord-52f347f56466453abe5f7dbf822a32cf
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455638B2

Reaction notes

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