Chloroacetonitrile → [2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenoxy]acetonitrile
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].Cl[CH2:24][C:25]#[N:26]>>[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:19])([F:20])[F:21])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[O:22][CH2:24][C:25]#[N:26]Participants
3
Procedure
2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol (50.0 mg, 0.16 mmol) was alkylated with chloroacetonitrile (24.6 μL, 29.4 mg, 0.39 mmol) as described in Example 47, affording[2-fluoro-5-(7-trifluoromethyl[1,8]-naphthyridin-4-yl)phenoxy]acetonitrile (33.4 mg, 59%). δH (400 MHz, CDCl3) 4.94 (2H, s), 7.23-7.29 (2H, m), 7.40 (1H, dd, J 8.2 and 10.6), 7.56 (1H, d, J 4.3), 7.85 (1H, d, J 8.6), 8.53 (1H, d, J 8.6), 9.28 (1H, d, J 4.7). m/z (ES+) 348 [MH]+.
Sources & evidence
- ORD record
- ord-c24a5774973c4a36bc5d512f35d92b38
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960598B2
Reaction notes
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