Sodium hydride → 2-(1-(4-[4-({2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]butyl)-1H-imidazol-2-yl)-1-ethanol

HRID 2084400Notes

Reaction equation

HRID 2084400 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:6]=[CH:7][N:8]=1.[H-].[Na+].Cl[CH2:23][C:24]1[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:27][CH:28]=1>>[F:37][C:34]1[CH:35]=[CH:36][C:31](/[CH:30]=[CH:29]/[C:26]2[O:27][CH:28]=[C:24]([CH2:23][O:19][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][N:5]4[CH:6]=[CH:7][N:8]=[C:4]4[CH2:3][CH2:2][OH:1])=[CH:18][CH:17]=3)[N:25]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazoleHCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 120948402-(1-(4-[4-({2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]butyl)-1H-imidazol-2-yl)-1-ethanolYield 84.1%

Procedure

Using 4-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol (391 mg), 65% oily sodium hydride (60 mg) and 4-(chloromethyl)-2-((E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazole (375 mg), the same reaction as Example 2 was carried out to yield the titled compound (583 mg).

Workup

  1. customthe same reaction as Example 2

Sources & evidence

ORD record
ord-3f76f7fdd1a74e43a2b373b599bb321c
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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