3-Acetylphenylboronic acid → 1-[2'-Fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]ethanone

HRID 1061824Notes

Reaction equation

HRID 1061824 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.[C:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)(=[O:32])[CH3:31]>>[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]=1[C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([C:30](=[O:32])[CH3:31])[CH:38]=1

Participants

3

Reactant 2

HCID 27343103-Acetylphenylboronic acidHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 101797471-[2'-Fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]ethanoneYield 60.2%

Procedure

Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) was coupled to 3-acetylphenyl-boronic acid (14.5 mg, 0.089 mmol) as described in Example 35 part c), affording 1-[2′-fluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]ethanone (16.8 mg, 60%). δH (360 MHz, CDCl3) 2.66 (3H, s), 7.39-7.44 (1H, dd, J 9.8 and 8.4), 7.47-7.52 (1H, m), 7.58-7.62 (3H, m), 7.80-7.85 (2H, m), 8.01 (1H, dt, J 7.7, 1.2), 8.18 (1H, d, J 1.4), 8.55 (1H, d, J 8.8), 9.30 (1H, d, J 4.6). m/z (ES+) 411 [MH]+.

Sources & evidence

ORD record
ord-6ced6fdd190f4399a590b65cd206ade8
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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