4-Methoxy-3-(trifluoromethyl)benzyl bromide → N-[4-[5-[[4-methoxy-3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-2-pyridyl]-3-phenylpropionamide

HRID 452758Notes

Reaction equation

HRID 452758 reaction equation
[SH:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:8]=2)=[N:4][N:3]=1.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][C:27]=1[C:34]([F:37])([F:36])[F:35]>>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][S:1][C:2]2[O:6][C:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:8]=3)=[N:4][N:3]=2)=[CH:28][C:27]=1[C:34]([F:35])([F:37])[F:36]

Participants

3

Reactant 2

HCID 27753024-Methoxy-3-(trifluoromethyl)benzyl bromideHCID 178520430HCID 178520430, compound

Product 1

HCID 68663695N-[4-[5-[[4-methoxy-3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-2-pyridyl]-3-phenylpropionamideYield 39%

Procedure

In the same manner as in Example 1 and using N-[4-(5-mercapto-1,3,4-oxadiazol-2-yl)-2-pyridyl]-3-phenylpropionamide instead of 5-(benzothiazol-6-yl)-1,3,4-oxadiazole-2-thiol and 4-methoxy-3-(trifluoromethyl)benzyl bromide instead of 3-(trifluoromethyl)benzyl chloride, the title compound (yield 39%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-5e1755496a0c4b218b62a0434ed18b7c
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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