5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10135167, compound

HRID 1061787Notes

Reaction equation

HRID 1061787 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:37])=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=3)[CH:28]=2)OC1>>[F:37][C:26]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:28][C:27]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285298HCID 22285298, compound

Product 1

HCID 10135167HCID 10135167, compoundYield 11%

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)-2′-fluorobiphenyl-3-carbonitrile (87 mg, 0.28 mmol) as described in Example 7 part g), affording 2′-fluoro-5′-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-3-carbonitrile (9 mg, 11%). δH (360 MHz, CDCl3) 7.41-7.46 (1H, m), 7.51-7.63 (4H, m), 7.72 (1H, d, J 7.7), 7.79-7.87 (2H, m), 7.91 (1H, d, J 1.1), 8.52 (1H, d, J 8.8), 9.30 (1H, d, J 4.2). m/z (ES+) 394 [MH]+.

Sources & evidence

ORD record
ord-1d24bef50d5c43bd9cd9e114f81e1038
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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