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

HRID 1610976Notes

Reaction equation

HRID 1610976 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[O:11][CH:12]=[C:13]([CH2:15]Cl)[N:14]=2)=[CH:4][CH:3]=1.[CH3:17][S:18]([CH2:21][C:22]1[N:23]([CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[CH:24]=[CH:25][N:26]=1)(=[O:20])=[O:19].[H-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[O:11][CH:12]=[C:13]([CH2:15][O:37][C:34]3[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][CH2:28][CH2:27][N:23]4[CH:24]=[CH:25][N:26]=[C:22]4[CH2:21][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:36][CH:35]=3)[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazoleHCID 222592974-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 222593282-[(E)-2-(4-fluorophenyl)ethenyl]-4-[[4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazoleYield 55.5%

Procedure

Using 2-[(E)-2-(4-fluorophenyl)ethenyl]-4-(chloromethyl)-1,3-oxazole (274 mg), 4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol (300 mg) and 65% sodium hydride (39.5 mg), the same reaction as Example 11-(i) was carried out to yield the titled compound (275 mg) as a colorless crystal powder.

Workup

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

Sources & evidence

ORD record
ord-d748408949894dd3b3ef59272150d82d
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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