2-Bromopyridine → 5-[4-Fluoro-3-(pyridin-2-yloxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine

HRID 1061832Notes

Reaction equation

HRID 1061832 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]=1[OH:22].Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=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[O:22][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 222853142-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol

Product 1

HCID 101106085-[4-Fluoro-3-(pyridin-2-yloxy)phenyl]-2-trifluoromethyl[1,8]naphthyridineYield 24.5%

Procedure

2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol (50.0 mg, 0.16 mmol) was alkylated with 2-bromopyridine (18.6 μL, 30.8 mg, 0.20 mmol) as described in Example 47, except that heating at 150° C. overnight was required, affording 5-[4-fluoro-3-(pyridin-2-yloxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine (15.1 mg, 24%). δH (400 MHz, CDCl3) 7.04-7.09 (2H, m), 7.30-7.35 (1H, m), 7.38-7.43 (2H, m), 7.60 (1H, d, J 4.7), 7.73-7.79 (1H, m), 7.83 (1H, d, J 8.6), 8.17 (1H, dd, J 5.1 and 2.0), 8.64 (1H, d, J 8.6), 9.27 (1H, d, J 4.3). m/z (ES+) 386 [MH]+.

Workup

  1. customheating at 150° C.
  2. customovernight

Sources & evidence

ORD record
ord-292c79b9f3f54e53af9304bc44c41656
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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