2,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid → 5-(2,4-Difluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061777Notes

Reaction equation

HRID 1061777 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)=[C:21]([F:29])[CH:20]=[CH:19][C:18]=1B(O)O>>[F:29][C:21]1[C:22]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[C:17]([F:16])[CH:18]=[CH:19][C:20]=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 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 102935605-(2,4-Difluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 34%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid (66 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(2,4-difluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (27 mg, 34%). δH (360 MHz, CDCl3) 7.28 (1H, m), 7.42-7.49 (2H, m), 7.63 (1H, d, J 4.6), 7.84-7.88 (2H, m), 8.35 (1H, dd, J 2.3 and 8.6), 8.69 (1H, dd, J 1.8 and 4.9), 8.80 (1H, s), 9.33 (1H, d, J 4.2). m/z (ES+) 388 [MH]+.

Sources & evidence

ORD record
ord-dc77f2e9b59447e1974cd8ef621c8a4f
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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