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

HRID 627550Notes

Reaction equation

HRID 627550 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.[F: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:36][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:27]([C:29]3[CH:30]=[N:31][C:32]([Cl:35])=[CH:33][CH:34]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=3)[OH:28])[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 2748413(3-Chlorophenyl)(pyridin-3-yl)methanoneHCID 497626942-Chloro-5-(3-fluorobenzoyl)pyridineHCID 867160566-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one2×

Product 1

HCID 74222220(4-Chloro-3-phenylquinolin-6-yl)(6-chloropyridin-3-yl)(3-fluorophenyl)methanol

Procedure

The title compound was prepared using 6-bromo-4-chloro-3-phenylquinoline (Intermediate 3, step c) and (3-fluorophenyl)(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), 8.30 (d, J=2.20 Hz, 1H), 8.10 (d, J=8.80 Hz, 1H), 7.68 (ddd, J=2.20, 8.62, 17.55 Hz, 2H), 7.46-7.54 (m, 5H), 7.33 (d, J=8.56 Hz, 2H), 7.05-7.11 (m, 3H); MS m/e 474.9 [M+H]+.

Sources & evidence

ORD record
ord-9274f4ecb7804b2381dc6332aafea067
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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