3-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acid → 5-[3-(3,5-Difluoropyridin-2-yl)-4-fluorophenyl]-2-trifluoromethyl[1,8]-naphthyridine

HRID 1061813Notes

Reaction equation

HRID 1061813 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[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[C:26]1[C:31]([F:32])=[CH:30][C:29]([F:33])=[CH:28][N:27]=1>>[F:32][C:31]1[C:26]([C:18]2[CH:19]=[C:20]([C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]4)[CH:21]=[CH:22][C:17]=2[F:16])=[N:27][CH:28]=[C:29]([F:33])[CH:30]=1

Participants

3

Reactant 2

HCID 116374193-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acidHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 102012705-[3-(3,5-Difluoropyridin-2-yl)-4-fluorophenyl]-2-trifluoromethyl[1,8]-naphthyridineYield 68%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 4-fluoro-3-(3,5-difluoropyridin-2-yl)phenylboronic acid (71 mg, 0.28 mmol) as described in Example 7 part g), affording 5-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-2-trifluoromethyl[1,8]-naphthyridine (59 mg, 68%). δH (360 MHz, CDCl3) 7.36-7.44 (2H, m), 7.55-7.62 (2H, m), 7.75 (1H, dd, J 2.3 and 6.5), 7.85 (1H, d, J 8.8), 8.48 (1H, d, J 2.1), 8.57 (1H, d, J 8.8), 9.28 (1H, d, J 4.2). m/z (ES+) 406 [MH]+.

Sources & evidence

ORD record
ord-85aafa06812042738f79d6e50c67c293
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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