5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 5-(2-Fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061771Notes

Reaction equation

HRID 1061771 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2.[F:16][C:17]1[C:22]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>>[F:16][C:17]1[C:22]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853162-Fluoro-3-(pyridin-3-yl)phenylboronic acid

Product 1

HCID 99474825-(2-Fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 45%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2-fluoro-3-(pyridin-3-yl)benzeneboronic acid (61 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(2-fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (36 mg, 45%). δH (360 MHz, CDCl3) 7.40-7.55 (3H, m), 7.65-7.70 (2H, m), 7.84 (1H, d, J 8.4), 7.93 (1H, dq, J 8.1 and 1.9), 8.37 (1H, dd, J 2.3 and 8.6), 8.67 (1H, dd, J 1.6 and 4.7), 8.86 (1H, s), 9.34 (1H, d, J 4.6). m/z (ES+) 370 [MH]+.

Sources & evidence

ORD record
ord-a1eb1cffe6294d7d9992a29556b86c1d
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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