6-Oxo-5-trifluoromethyl-1,6-dihydro-pyridine-2-carboxylic acid methyl ester synthesis
- Product Name:6-Oxo-5-trifluoromethyl-1,6-dihydro-pyridine-2-carboxylic acid methyl ester
- CAS Number:1006364-88-0
- Molecular formula:C8H6F3NO3
- Molecular Weight:221.13
1415899-18-1
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Yield: 40%
Reaction Conditions:
with trifluoroacetic anhydride in N,N-dimethyl-formamide at 0 - 50; for 6 h;
Steps:
[00174] Trifluoroacetic anhydride (0.4 mL, 2.3 mmol) was added dropwise to a mixture of 57 (50 mg, 0.23 mmol) in DMF (1 mL) at 0 °C for 3.5 h. The reaction mixture was stirred at45-50 °C for 2.5 h. The mixture was poured into ice-water (10 mL) and adjusted to pH 5-6 with 30% sodium hydroxide solution. The mixture was extracted with ethyl acetate (5 mL X3). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated under reduced pressure to afford 58 (20 mg, 40%) as a white solid, which was used for the next step directly without further purification. ‘H NMR (CDC13): 5 7.90 (d, J = 6.8 Hz, 1H), 7.02 (d, J= 6.8 Hz, 1H), 4.04 (s, 3H).
References:
VITAE PHARMACEUTICALS, INC.;CLAREMON, David, A.;DILLARD, Lawrence, Wayne;DONG, Chengguo;FAN, Yi;JIA, Lanqi;LOTESTA, Stephen, D.;MARCUS, Andrew;SINGH, Suresh, B.;TICE, Colin, M.;YUAN, Jing;ZHAO, Wei;ZHENG, Yajun;ZHUANG, Linghang WO2014/179564, 2014, A1 Location in patent:Paragraph 00174
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1000210-73-0
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