(3-Acetamidophenyl)boronic acid → N-[2'-fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]acetamide

HRID 1061823Notes

Reaction equation

HRID 1061823 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]([NH:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:31]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:20])([F:19])[F:21])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:6][C:7]=1[C:36]1[CH:37]=[CH:38][CH:39]=[C:34]([NH:33][C:30](=[O:32])[CH3:31])[CH:35]=1

Participants

3

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 10273961N-[2'-fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]acetamideYield 41.5%

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-acetamidophenyl-boronic acid (15.9 mg, 0.089 mmol) as described in Example 35 part c), affording N-[2′-fluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-3-yl]acetamide (12.0 mg, 41%). δH (360 MHz, CDCl3) 2.20 (3H, s), 7.35-7.47 (5H, m), 7.54-7.60 (2H, m), 7.84 (1H, d, J 8.4), 7.87 (1H, s), 8.56 (1H, d, J 8.8), 9.28 (1H, d, J 4.6). m/z (ES+) 426 [MH]+.

Sources & evidence

ORD record
ord-43a692eb50194fec87f56e60ef7d0ee5
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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