5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 4-Fluoro-3'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile

HRID 1061765Notes

Reaction equation

HRID 1061765 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:18]=[C:19]([C:38]#[N:39])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=2)=[CH:21][CH:22]=1>>[F:16][C:17]1[CH:18]=[C:19]([C:38]#[N:39])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([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]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853364-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 102718744-Fluoro-3'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrileYield 26%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 4-fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (91 mg, 0.28 mmol) as described in Example 7 part g), affording 4-fluoro-3′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile (22 mg, 26%). δH (360 MHz, CDCl3) 7.39-7.45 (1H, m), 7.51-7.76 (7H, m), 7.87 (1H, d, J 8.4), 8.71 (1H, d, J 8.4), 9.29 (1H, d, J 4.6). m/z (ES+) 394 [MH]+.

Sources & evidence

ORD record
ord-3abab51cfbe9452eb8b88115a8ce4e21
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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