Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride) → 5-(4-Fluoro-3-quinolin-6-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061827Notes

Reaction equation

HRID 1061827 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[C:39]2[C:34](=[CH:35][C:36](B(O)O)=[CH:37][CH:38]=2)[CH:33]=[CH: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:21])([F:20])[F:19])=[N:13]3)=[CH:4][C:3]=1[C:36]1[CH:35]=[C:34]2[C:39](=[CH:38][CH:37]=1)[N:30]=[CH:31][CH:32]=[CH:33]2

Participants

3

Reactant 2

HCID 4192671Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride)HCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 102022045-(4-Fluoro-3-quinolin-6-ylphenyl)-2-trifluoromethyl[1,8]naphthyridineYield 61%

Procedure

Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) was coupled to 6-quinolinylboronic acid (15.3 mg, 0.089 mmol) as described in Example 35 part c), affording 5-(4-fluoro-3-quinolin-6-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (17.4 mg, 61%). δH (400 MHz, CDCl3) 7.43-7.57 (3H, m), 7.64 (1H, d, J 4.3), 7.69-7.72 (1H, m), 7.85 (1H, d, J 8.6), 7.97 (1H, dt, J 8.6 and 1.8), 8.06 (1H, s), 8.22 (2H, d, J 8.2), 8.59 (1H, d, J 8.6), 8.98 (1H, dd, J 1.8 and 4.1), 9.30 (1H, d, J 4.3). m/z (ES+) 420 [MH]+.

Sources & evidence

ORD record
ord-d1db6625747d44d28585c0620f7512b4
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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