(6-[4-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-3-YL)METHANOL synthesis

5synthesis methods

Product Name:(6-[4-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-3-YL)METHANOL
CAS Number:356058-13-4
Molecular formula:C13H10F3NO
Molecular Weight:253.22

3-PYRIDINECARBOXYLIC ACID, 6-[4-(TRIFLUOROMETHYL)PHENYL]-, METHYL ESTER

356058-34-9
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(6-[4-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-3-YL)METHANOL

356058-13-4
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Yield:356058-13-4 75%

Reaction Conditions:

with diisobutylaluminium hydride in dichloromethane;toluene at -78; for 1 h;Inert atmosphere;

Steps:

Intermediate A4 5-Hydroxymethyl-2-(4-trifluoromethylphenyl)pyridine

5-Hydroxymethyl-2-(4-trifluoromethylphenyl)pyridine
A solution of Intermediate A20 (4.63 g) in dry dichloromethane (100 ml) was cooled to -78° C. under argon, then DIBAL-H (26.7 ml, 1.5M solution in toluene) was added dropwise over 20 min.
Stirring was continued for 40 min at -78° C., then 2M hydrochloric acid (52 ml) was added dropwise over 15 min.
The solution was allowed to warm slowly to room temperature, then the organic layer was separated, washed with water, dried and evaporated.
Chromatography (silica, 1:1 ethyl acetate/hexane) gave the product as a white solid (3.03 g, 75%).
¹H-NMR (CDCl₃) δ 1.85 (1H,t), 4.81 (2H,d), 7.75 (2H,m), 7.83 (1H,dd), 8.11 (1H,d), 8.72 (1H,m); MS (APCI+) found (M+1)=254, C₁₃H₁₀F₃NO requires 253.

References:

US9266841,2016,B2 Location in patent:Page/Page column 15

21543-49-7 Synthesis