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

HRID 2084410Notes

Reaction equation

HRID 2084410 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]([F:38])=[CH:34][C:33]=2[F:39])[O:28][CH:29]=1>>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1/[CH:31]=[CH:30]/[C:27]1[O:28][CH:29]=[C:25]([CH2:24][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[CH:15]=[CH:14][N:13]=[C:12]3[CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH:5]=[CH:6][CH:7]=2)[N:26]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 12109498(E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazoleHCID 227333623-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl)-1,2-propanediol

Product 1

HCID 227333693-(1-{3-[3-({2-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]propyl}1H-imidazol-2-yl)-1,2-propanediolYield 60.4%

Procedure

Using 3-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl}-1,2-propanediol (203 mg), 65% oily sodium hydride (29 mg) and 4-(chloromethyl)-2-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazole (197 mg), the same reaction as Example 2 was carried out to yield the titled compound (220 mg).

Workup

  1. customthe same reaction as Example 2

Sources & evidence

ORD record
ord-f7ba0e5b03444386bc6aa59a19c0d86f
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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