5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10155992, compound

HRID 1061802Notes

Reaction equation

HRID 1061802 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](B(O)O)=[CH:19][C:18]=1[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][N:27]=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:26]1[CH:31]=[CH:30][N:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285299HCID 22285299, compound

Product 1

HCID 10155992HCID 10155992, compoundYield 25%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 4-fluoro-3-pyrimidin-4-yl-phenylboronic acid (61 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(4-fluoro-3-pyrimidin-4-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (20 mg, 25%). δH (360 MHz, CDCl3) 7.46 (1H, dd, J 8.4 and 11.2), 7.60-7.64 (2H, m), 7.85 (1H, d, J 8.8), 7.96-7.98 (1H, m), 8.42 (1H, dd, J 2.5 and 7.4), 8.53 (1H, d, J 8.4), 8.87 (1H, d, J 5.3), 9.30 (1H, s), 9.31 (1H, s). m/z (ES+) 371 [MH]+.

Sources & evidence

ORD record
ord-da215aaa56394cc48c7a4ff350acd11b
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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