5'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2'-difluorobiphenyl-2-carbonitrile → 5,2'-Difluoro-5'-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile

HRID 1061763Notes

Reaction equation

HRID 1061763 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.CC1(C)COB([C:23]2[CH:24]=[CH:25][C:26]([F:38])=[C:27]([C:29]3[C:30]([C:36]#[N:37])=[CH:31][CH:32]=[C:33]([F:35])[CH:34]=3)[CH:28]=2)OC1>>[F:35][C:33]1[CH:34]=[C:29]([C:27]2[CH:28]=[C:23]([C:2]3[C:3]4[C:8](=[N:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:24]=[CH:25][C:26]=2[F:38])[C:30]([C:36]#[N:37])=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 116884435'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2'-difluorobiphenyl-2-carbonitrileHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 101363065,2'-Difluoro-5'-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrileYield 30%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2′-difluorobiphenyl-2-carbonitrile (91 mg, 0.28 mmol) as described in Example 7 part g), affording 5,2′-difluoro-5′-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile (27 mg, 30%). δH (360 MHz, CDCl3) 7.24-7.29 (1H, m), 7.34 (1H, dt, J 7.2 and 1.9), 7.46-7.51 (1H, m), 7.59-7.65 (3H, m), 7.84-7.90 (2H, m), 8.68 (1H, d, J 8.8), 9.29 (1H, d, J 4.2). m/z (ES+) 412 [MH]+.

Sources & evidence

ORD record
ord-78ce55425ad5469794c89d969f8bd5d8
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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