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

HRID 2084406Notes

Reaction equation

HRID 2084406 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH2:17][CH:18]([OH:21])[CH2:19][OH:20])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:25][C:26]1[N:27]=[C:28](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[O:29][CH:30]=1>>[F:39][C:36]1[CH:37]=[CH:38][C:33](/[CH:32]=[CH:31]/[C:28]2[O:29][CH:30]=[C:26]([CH2:25][O:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]4[CH:16]=[CH:15][N:14]=[C:13]4[CH2:17][CH:18]([OH:21])[CH2:19][OH:20])=[CH:4][CH:3]=3)[N:27]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazoleHCID 121098723-{1-[4-(4-hydroxyphenyl)butyl]-1H-imidazol-2-yl)-1,2-propanediol

Product 1

HCID 121094963-(1-{4-[4-({2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]butyl}-1H-imidazol-2-yl)-1,2-propanediolYield 70.4%

Procedure

Using 3-{1-[4-(4-hydroxyphenyl)butyl]-1H-imidazol-2-yl}-1,2-propanediol (291 mg), 65% oily sodium hydride (39 mg) and 4-(chloromethyl)-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazole (250 mg), the same reaction as Example 2 was carried out to yield the titled compound (347 mg).

Workup

  1. customthe same reaction as Example 2

Sources & evidence

ORD record
ord-640550e6a1534bcdb4f2e1be5e4ccadc
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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