(4-Methoxyphenyl)-3-pyridinylmethanone → (4-Chloro-3-phenylquinolin-6-yl)(4-methoxyphenyl)pyridin-3-ylmethanol

HRID 627548Notes

Reaction equation

HRID 627548 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:5]2O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[O:29])=[CH:24][CH:23]=1.[Cl:36]C1C=C(C(C2C=NC=CC=2)=O)C=CC=1>>[Cl:36][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:28]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=3)([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)[OH:29])[CH:3]=2)[N:8]=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 32108(4-Methoxyphenyl)-3-pyridinylmethanoneHCID 2748413(3-Chlorophenyl)(pyridin-3-yl)methanoneHCID 867160566-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one2×

Product 1

HCID 74222137(4-Chloro-3-phenylquinolin-6-yl)(4-methoxyphenyl)pyridin-3-ylmethanol

Procedure

The title compound was prepared using 6-bromo-4-chloro-3-phenylquinoline (Intermediate 3, step c) and (4-methoxyphenyl)(pyridin-3-yl)methanone in place of 6-bromo-2,4-dichloro-3-phenylquinoline and (3-chlorophenyl)(pyridin-3-yl)methanone, respectively, according to the procedure described in Example 25. 1H NMR (400 MHz, CDCl3) δ 8.81 (s, 1H), 8.60-8.68 (m, 1H), 8.51-8.57 (m, 1H), 8.38 (d, J=1.96 Hz, 1H), 8.08 (d, J=8.80 Hz, 1H), 7.67-7.78 (m, 2H), 7.44-7.57 (m, 5H), 7.25-7.32 (m, 1H), 7.20 (d, J=8.80 Hz, 2H), 6.88 (d, J=8.80 Hz, 2H), 3.81 (s, 3H); MS m/e 452.9 [M+H]+.

Sources & evidence

ORD record
ord-cb37325e7ba4465d922a5049df93d270
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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