2,3,4-Trifluorobenzoic acid → HCID 12135109, compound

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Reaction Steps

2,3,4-Trifluorobenzoic acid and the product of Example 5, Step A, 2-fluoro-4-(3-methoxy-1-propynyl)aniline, were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1. After workup, followed by purification by chromatography on silica gel (10% EtOAc/hexanes as eluant), 3,4-difluoro-2-[[2-fluoro-4-(3-methoxy-1-propynyl)phenyl]amino]-benzoic acid was isolated (62%) as a pale yellow solid; mp (EtOAc/hexanes) 221-223° C. 1H NMR [400 MHz, (CD3)2SO] δ 13.60 (br s, 1 H), 9.27 (br s, 1 H), 7.85-7.79 (m, 1 H,), 7.36 (dd, J=12.0, 1.8 Hz, 1 H), 7.20 (dd, J=8.3, 1.5 Hz, 1 H), 7.18-7.11 (m, 1 H), 6.96 (td, 8.8, 5.5 Hz, 1 H), 4.31 (s, 2 H), 3.32 (s, 3 H). Anal Calcd for C17 H12F3NO3: C, 60.9; H, 3.6; N, 4.2. Found C, 61.4; H, 3.6; N, 4.2.

Provenance & Evidence