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Monday, 13 February 2017

(5-Chloro-2-methoxyphenyl)[3-fluoro-5-(trifluoromethyl)phenyl]methanone

str1
Cas 329941-92-6
(5-Chloro-2-methoxyphenyl)[3-fluoro-5-(trifluoromethyl)phenyl]methanone (7)
7 as white crystals
 
mp 93–95 °C;
 
1H NMR (500 MHz, CDCl3) 7.82 (s, 1H), 7.66 (d, J = 8.5 Hz, 1H), 7.53 (d, J =7.5 Hz, 1H), 7.49 (d, J = 9.0 Hz, 1H), 7.42 (s, 1H), 6.97 (d, J = 9.0 Hz, 1H), 3.71 (s, 3H);
 
13C NMR (500 MHz, CDCl3) 192.1, 162.4 (d, J = 249.3 Hz), 156.0, 140.4 (d, J = 6.4 Hz), 132.8, 132.7 (dq, J = 7.5, 33.6 Hz), 129.7, 128.4, 126.3, 122.9 (q, J = 272.3), 122.1 (m), 119.5 (d, J = 22.4), 116.9 (m), 113.3, 55.3;
 
HRMS calculated for C15H9ClF4O2 [M + H]+: 333.0299, Found: 333.0306.
 
Abstract Image
A convergent synthesis of NNRTI 1 is described. The key step involves a direct coupling of acid chloride 4 with Grignard reagent 11 in the presence of bis[2-(N,N-dimethylamino)ethyl] ether that moderates the reactivity of the Grignard reagent to give benzophenone 7. An efficient 2-step process for the preparation of 2-fluoro-3-methyl-4-aminobenzoic acid (3) is also described.

Practical Synthesis of A Benzophenone-Based NNRT Inhibitor of HIV-1

 Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, United States
 Boehringer Ingelheim (Canada) Ltd., Research and Development, 2100 Cunard Street, Laval, Québec H7S 2G5, Canada
Org. Process Res. Dev.201216 (4), pp 561–566
DOI: 10.1021/op200301h
 
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