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

HRID 1610967Notes

Reaction equation

HRID 1610967 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:7]=[CH:8][N:9]=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:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][N:6]3[CH:7]=[CH:8][N:9]=[C:5]3[CH2:4][CH2:3][S:2][CH3:1])=[CH:15][CH:16]=2)[N:26]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 12109498(E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazoleHCID 222593154-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 222593442-[(E)-2-(2,4-difluorophenyl)ethenyl]-4-[[4-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazoleYield 92.6%

Procedure

Using 4-[4-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenol (500 mg), 65% sodium hydride (69.8 mg) and 4-chloromethyl-2-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazole (483 mg), the same reaction as Example 11-(i) was carried out to yield the titled compound (812 mg) as a colorless amorphous form.

Workup

  1. customthe same reaction as Example 11-(i)

Sources & evidence

ORD record
ord-7eda427bc4c44570995a7074bf58311e
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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