2-Methoxyphenylboronic acid → 5-(6-Fluoro-2'-methoxybiphenyl-3-yl)-2-trifluoromethyl[1,8]-naphthyridine

HRID 1061825Notes

Reaction equation

HRID 1061825 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.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O>>[F:1][C:2]1[C:3]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[O:31][CH3:30])=[CH:4][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:20])([F:21])[F:19])=[N:13]3)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 101354765-(6-Fluoro-2'-methoxybiphenyl-3-yl)-2-trifluoromethyl[1,8]-naphthyridineYield 53.5%

Procedure

Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) was coupled to 2-methoxyphenyl-boronic acid (13.5 mg, 0.089 mmol) as described in Example 35 part c), affording 5-(6-fluoro-2′-methoxybiphenyl-3-yl)-2-trifluoromethyl[1,8]-naphthyridine (14.5 mg, 53%). δH (360 MHz, CDCl3) 3.86 (3H, s), 7.03-7.09 (2H, m), 7.32-7.48 (4H, m), 7.55 (1H, dd, J 2.5 and 6.7), 7.60 (1H, d, J 4.6), 7.83 (1H, d, J 8.4), 8.66 (1H, d, J 8.4), 9.27 (1H, d, J 4.6). m/z (ES+) 399 [MH]+.

Sources & evidence

ORD record
ord-ddd180efb73e457fa1e8934d24b25e80
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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