Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 58491079, compound

HRID 660446Notes

Reaction equation

Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(C(C)C)CC)(C)C.[CH:19]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([N:32]3[C:36]([C:37]([F:40])([F:39])[F:38])=[N:35][N:34]=[C:33]3[SH:41])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1>CN(C=O)C>[CH:19]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([N:32]3[C:36]([C:37]([F:38])([F:40])[F:39])=[N:35][N:34]=[C:33]3[S:41][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:24][CH:23]=2)[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 2-bromo-2-methylpropanoate (89 μL, 0.596 mmol) and diisopropylethylamine (0.31 mL, 1.789 mmol) were added to a solution of 4-(4-cyclopropylnaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazole-3-thiol (0.2 g, 0.596 mmol) in DMF (1.2 mL) and the mixture heated at 60° C. for 20 hours. The mixture was concentrated, acidified with HCl (1M aqueous, 2 mL) and extracted with ethyl acetate (3×3 mL). The combined organic extracts were dried over sodium sulfate, concentrated and purified by column chromatography (0-25% EtOAc/hexanes) to provide ethyl 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate as a clear oil (0.1 g, 37%).

Workup

concentrationThe mixture was concentrated
extractionextracted with ethyl acetate (3×3 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated
custompurified by column chromatography (0-25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-48c6c145431e4329bb1230104d556cc0
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084483B2

Reaction notes

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