4-Methoxybenzaldehyde → (6-Methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanol

HRID 456991Notes

Reaction equation

HRID 456991 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2.[Li]C(C)(C)C.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>C1COCC1.CCCCC>[CH3:13][O:12][C:11]1[C:2]([CH:27]([C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[OH:28])=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([S:14][CH3:15])[CH:5]=[CH:4]2

Participants

6

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 221396965-Bromo-6-methoxy-2-methylthioquinolineHCID 178418306HCID 178418306, compound

Product 1

HCID 22139702(6-Methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanolYield 35%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 280 mg (1 mmole) of 5-bromo-6-methoxy-2-methylsulfanyl-quinoline in 4 mL THF was cooled to −78° C. and treated with 1.5 mL of 1.5 M t-BuLi in pentane. After stirring for 1.5 hours, 1.5 eq of p-methoxybenzaldehyde was added and the reaction allowed to warm to room temperature. After partitioning between EtOAc and water the product was purified by chromatography on silica gel (1:3 EtOAc/hexane) to afford (6-methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanol (120 mg, 35%).

Workup

  1. customAfter partitioning between EtOAc and water the product
  2. customwas purified by chromatography on silica gel (1:3 EtOAc/hexane)

Sources & evidence

ORD record
ord-bb862bdb97764221a6f63b57acf04191
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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