2-Bromo-5-fluoropyridine → 2-((3-fluorophenoxy)methyl)-6-(5-fluoropyridin-2-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[N:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20]C=3)[CH2:11][CH2:10][C:9]=2[N:8]=1.FC1C=C(C=CC=1)OCC1C=CC2C(=O)NCCC=2[N:35]=1.BrC1C=CC(F)=CN=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[N:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:35]=3)[CH2:11][CH2:10][C:9]=2[N:8]=1Participants
4
Reactant 3
Product 1
Procedure
Prepared in a manner similar to the preceding example, 2-((3-fluorophenoxy)methyl)-6-(4-fluorophenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, using the common intermediate 2-((3-fluorophenoxy)methyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one as described above and 2-bromo-5-fluoropyridine. 1H NMR (400 MHz, CDCl3) δ 8.49 (1H, d, J=8), 8.32 (1H, d, J=3), 8.03 (1H, dd, J=9.2, 4.0), 7.60 (1H, d, 8), 7.54 (1H, dd, J=23, 8), 7.28 (1H, dd, J=16, 7.6), 6.80 (1H, dd, 7.6, 1.6), 6.74 (1H, ddd, J=23, 8.0, 1.6), 5.26 (1H, s), 4.41 (2H, t, J=6.8), 3.38 (2H, t, J=6.8); LC-MS (M+H)=368.2.
Sources & evidence
- ORD record
- ord-e495aa5ab94349fdac46e635ae279e9d
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853237B2
Reaction notes
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