3-(Bromomethyl)quinolin-2(1H)-one → 2-[1-Methoxy-1-[3-methoxy-4-(1,2-dihydro-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole

HRID 1974512Notes

Reaction equation

HRID 1974512 reaction equation
Br[CH2:2][C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)([O:24][CH3:25])[CH2:22][CH3:23])=[CH:17][C:16]=1[O:31][CH3:32]>>[CH3:25][O:24][C:21]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:2][C:3]2[C:4](=[O:13])[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[C:16]([O:31][CH3:32])[CH:17]=1)[CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 3367063-(Bromomethyl)quinolin-2(1H)-oneHCID 191016292-[1-(4-Hydroxy-3-methoxyphenyl)-1-methoxypropyl]thiazole

Product 1

HCID 191016312-[1-Methoxy-1-[3-methoxy-4-(1,2-dihydro-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazoleYield 28%

Procedure

Using a similar procedure to that described in Example 1, 3-bromomethyl-1,2-dihydroquinolin-2-one was reacted with 2-[1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropyl]thiazole to give 2-[1-methoxy-1-[3-methoxy-4-(1,2-dihydro-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole in 28% yield, m.p. 170°-171° C. (recrystallised from a mixture of hexane and ethyl acetate).

Sources & evidence

ORD record
ord-b5b87a56d2704974b3cc1afae768aace
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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