(3-Chlorophenyl)(pyridin-3-yl)methanone → (3-Chlorophenyl)(4-chloro-3-phenylquinolin-6-yl)(6-chloropyridin-3-yl)methanol

HRID 627549Notes

Reaction equation

HRID 627549 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.[Cl:20][C:21]1[CH:22]=[C:23]([C:27]([C:29]2[CH:30]=[N:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[O:28])[CH:24]=[CH:25][CH:26]=1.[Cl:36]C1C=C(C(C2C=NC=CC=2)=O)C=CC=1>>[Cl:20][C:21]1[CH:22]=[C:23]([C:27]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]3[Cl:36])([C:29]2[CH:30]=[N:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[OH:28])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 2748413(3-Chlorophenyl)(pyridin-3-yl)methanoneHCID 497626965-(3-Chlorobenzoyl)-2-chloropyridineHCID 867160566-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one2×

Product 1

HCID 74222139(3-Chlorophenyl)(4-chloro-3-phenylquinolin-6-yl)(6-chloropyridin-3-yl)methanol

Procedure

The title compound was prepared using 6-bromo-4-chloro-3-phenylquinoline (Intermediate 3, step c) and (3-chlorophenyl)(6-chloropyridin-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), 8.40 (d, J=2.69 Hz, 1H), 8.29 (d, J=2.20 Hz, 1H), 8.10 (d, J=9.05 Hz, 1H), 7.70 (dd, J=2.69, 8.31 Hz, 1H), 7.65 (dd, J=2.08, 8.93 Hz, 1H), 7.47-7.54 (m, 5H), 7.37 (d, J=1.47 Hz, 1H), 7.31-7.35 (m, 3H), 7.18 (dt, J=1.80, 7.15 Hz, 1H); MS m/e 490.8 [M+H]+.

Sources & evidence

ORD record
ord-a6ead071bbf2477286fad4be2747b7f8
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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