Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate → Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-oxo-ethylsulfanyl)-benzoate

HRID 512926Notes

Reaction equation

HRID 512926 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=3)[N:23]=2)[CH:15]=1)[OH:13].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=3)[N:23]=2)[CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 86720738Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 86720739Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-oxo-ethylsulfanyl)-benzoateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of hydroxy compound 46 (10.0 g, 0.021 mol) in dichloromethane (100 ml) was added in single lot pyridinium chlorochromate (13.44 g, 0.035 mol) and allowed to stir at ambient temperature for 2 hours. The resulting mixture was filtered through a bed of highflow. The residue was washed with dichloromethane (500 ml). The combined filtrate layer was evaporated and subjected to FC to give pale yellow solid 47 (8.0 g, 80%).

Workup

  1. filtrationThe resulting mixture was filtered through a bed of highflow
  2. washThe residue was washed with dichloromethane (500 ml)
  3. customThe combined filtrate layer was evaporated

Sources & evidence

ORD record
ord-e92d7dd0ac934bf9a21029b0f5542e32
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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