5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 9947481, compound

HRID 1061768Notes

Reaction equation

HRID 1061768 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][CH:26]=[CH:25][N:24]=2)=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>>[F:16][C:17]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=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 22285289HCID 22285289, compound

Product 1

HCID 9947481HCID 9947481, compoundYield 21%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2-fluoro-3-(pyridin-2-yl)benzeneboronic acid (61 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(2-fluoro-3-pyridin-2-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (17 mg, 21%). δH (360 MHz, CDCl3) 7.30-7.36 (1H, m), 7.42-7.55 (2H, m), 7.66 (1H, d, J 4.2), 7.77-7.83 (3H, m), 8.19 (1H, td, J 7.6 and 2.1), 8.38 (1H, dd, J 2.3 and 8.6), 8.78 (1H, dt, J 4.9 and 1.4), 9.33 (1H, d, J 4.2). m/z (ES+) 370 [MH]+.

Sources & evidence

ORD record
ord-04b0b4dd8a5a4e3c8ff255f57473b887
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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