(Pyrimidin-5-yl)boronic acid → 5-(4-Fluoro-3-pyrimidin-5-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061826Notes

Reaction equation

HRID 1061826 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][C:14]([C:18]([F:19])([F:20])[F:21])=[N:13]3)=[CH:4][C:3]=1[C:34]1[CH:35]=[N:30][CH:31]=[N:32][CH:33]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 101096895-(4-Fluoro-3-pyrimidin-5-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 41%

Procedure

Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) was coupled to 5-pyrimidinylboronic acid (prepared as described in WO 9411372; 11.0 mg, 0.089 mmol) as described in Example 35 part c), affording 5-(4-fluoro-3-pyrimidin-5-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (10.3 mg, 41%). δH (360 MHz, CDCl3) 7.49 (1H, t, J 9.5), 7.55-7.61 (3H, m), 7.86 (1H, d, J 8.4), 8.51 (1H, d, J 8.4), 9.01 (2H, d, J 1.1), 9.28 (1H, s), 9.32 (1H, d, J 4.6). m/z (ES+) 371 [MH]+.

Sources & evidence

ORD record
ord-5112c08f0c6e4ee49f1497a00bb6a4ca
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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