5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 5-(2-Fluoro-3-pyridin-4-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061774Notes

Reaction equation

HRID 1061774 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:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>>[F:16][C:17]1[C:22]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[CH:21][CH:20]=[CH:19][C:18]=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 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285310[2-Fluoro-3-(pyridin-4-yl)phenyl]boronic acid

Product 1

HCID 102704285-(2-Fluoro-3-pyridin-4-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 47%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2-fluoro-3-(pyridin-4-yl)benzeneboronic acid (61 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(2-fluoro-3-pyridin-4-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (37 mg, 47%). δH (360 MHz, CDCl3) 7.45-7.54 (4H, m), 7.65 (1H, d, J 4.2), 7.68-7.74 (1H, m), 7.84 (1H, d, J 8.4), 8.35 (1H, dd, J 2.5 and 8.8), 8.72-8.74 (2H, m), 9.34 (1H, d, J 4.2). m/z (ES+) 370 [MH]+.

Sources & evidence

ORD record
ord-a4ccf65aa851485288f03b755ac01bb5
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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