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

HRID 2084408Notes

Reaction equation

HRID 2084408 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:24][C:25]1[N:26]=[C:27](/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[O:28][CH:29]=1>>[F:41][C:38]([F:39])([F:40])[C:35]1[CH:36]=[CH:37][C:32](/[CH:31]=[CH:30]/[C:27]2[O:28][CH:29]=[C:25]([CH2:24][O:1][C:2]3[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]4[CH:15]=[CH:14][N:13]=[C:12]4[CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH:5]=[CH:6][CH:7]=3)[N:26]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 98571264-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleHCID 227333623-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl)-1,2-propanediol

Product 1

HCID 227333743-[1-(3-{3-[(2-{(E)-2-[4-(trifluoromethyl)phenyl]ethenyl}-1,3-oxazol-4-yl)methoxy]phenyl]propyl)-1H-imidazol-2-yl]-1,2-propanediolYield 68.9%

Procedure

Using 3-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl}-1,2-propanediol (194 mg), 65% oily sodium hydride (28 mg) and 4-(chloromethyl)-2-{(E)-2-[4-(trifluoromethyl)phenyl]ethenyl}-1,3-oxazole (212 mg), the same reaction as Example 2 was carried out to yield the titled compound (255 mg).

Workup

  1. customthe same reaction as Example 2

Sources & evidence

ORD record
ord-b0fa6fe34a334ecaa385a2d7c3146385
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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