3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → 5-(4-Fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061748Notes

Reaction equation

HRID 1061748 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:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][C:18]=1[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]3)=[CH:19][C:18]=1[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 101096225-(4-Fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 28.3%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (200 mg, 0.86 mmol) was coupled to 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine (349 mg, 1.2 mmol) as described in Example 3 part g), affording 5-(4-fluoro-3-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (90 mg, 28%). δH (360 MHz, CDCl3) 7.41-7.46 (2H, m), 7.50-7.55 (1H, m), 7.57-7.61 (2H, m), 7.85 (1H, d, J 8.4), 7.91-7.96 (1H, m), 8.55 (1H, d, J 8.8), 8.68 (1H, dd, J 1.4 and 4.9), 8.86 (1H, s), 9.30 (1H, d, J 4.6). m/z (ES+) 370 [MH]+.

Sources & evidence

ORD record
ord-a09abeb205f0469ea09b2aeae107d9df
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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