Sodium hydride → 2-[(E)-2-(2,6-difluorophenyl)ethenyl]-4-[[4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazole

HRID 1610979Notes

Reaction equation

HRID 1610979 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5](/[CH:8]=[CH:9]/[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[O:6][CH:7]=1.[CH3:18][S:19]([CH2:22][C:23]1[N:24]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)[CH:25]=[CH:26][N:27]=1)(=[O:21])=[O:20].[H-].[Na+]>>[F:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1/[CH:9]=[CH:8]/[C:5]1[O:6][CH:7]=[C:3]([CH2:2][O:38][C:35]2[CH:34]=[CH:33][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][N:24]3[CH:25]=[CH:26][N:27]=[C:23]3[CH2:22][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:37][CH:36]=2)[N:4]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 222592924-chloromethyl-2-[(E)-2-(2,6-difluorophenyl)ethenyl]-1,3-oxazoleHCID 222592974-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 222593532-[(E)-2-(2,6-difluorophenyl)ethenyl]-4-[[4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazoleYield 65.5%

Procedure

Using 4-(chloromethyl)-2-[(E)-2-(2,6-difluorophenyl)ethenyl]-1,3-oxazole (228 mg), 4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol (250 mg). and 65% sodium hydride (32.9 mg), the same reaction as Example 11-(i) was carried out to yield the titled compound (280 mg) as colorless needle crystals.

Sources & evidence

ORD record
ord-5f0a82879f264800864e2e07ce5ebcc6
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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