2-(Bromomethyl)quinoline → 2-[1-Methoxy-1-[3-methoxy-4-(quinol-2-ylmethoxy)phenyl]propyl]thiazole

HRID 1534392Notes

Reaction equation

HRID 1534392 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)([O:23][CH3:24])[CH2:21][CH3:22])=[CH:16][C:15]=1[O:30][CH3:31]>>[CH3:24][O:23][C:20]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[C:15]([O:30][CH3:31])[CH:16]=1)[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 124174182-(Bromomethyl)quinolineHCID 191016292-[1-(4-Hydroxy-3-methoxyphenyl)-1-methoxypropyl]thiazole

Product 1

HCID 191016572-[1-Methoxy-1-[3-methoxy-4-(quinol-2-ylmethoxy)phenyl]propyl]thiazoleYield 52%

Procedure

Using a similar procedure to that described in Example 1, 2-bromomethylquinoline was reacted with 2-[1 -(4-hydroxy-3-methoxyphenyl)-1-methoxypropyl]thiazole to give 2-[1-methoxy-1-[3-methoxy-4-(quinol-2-ylmethoxy)phenyl]propyl]thiazole in 52% yield, m.p. 100°-102° C. (recrystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and methylene chloride).

Sources & evidence

ORD record
ord-c9dd46357f8e4f7ba6cd4bc38718a75e
Source dataset
uspto-grants-1992_02
Patent number
US05089495

Reaction notes

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