HCID 11336372, compound → 4,2'-Difluoro-5'-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile

HRID 1061761Notes

Reaction equation

HRID 1061761 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][C:32]([F:35])=[CH:33][CH:34]=3)[CH:28]=2)OC1>>[F:35][C:32]1[CH:31]=[C:30]([C:36]#[N:37])[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])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 11336372HCID 11336372, compoundHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 102016644,2'-Difluoro-5'-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrileYield 14.4%

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)-4,2′-difluorobiphenyl-2-carbonitrile (77 mg, 0.24 mmol) as described in Example 7 part g), affording 4,2′-difluoro-5′-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile (13 mg, 14%). δH (400 MHz, CDCl3) 7.41-7.49 (2H, m), 7.54-7.63 (5H, m), 7.88 (1H, d, J 9.0), 8.68 (1H, d, J 8.2), 9.29 (1H, d, J 4.3). m/z (ES+) 412 [MH]+.

Sources & evidence

ORD record
ord-014fa46e9b3f41f991eeb8cd09b614cc
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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