Sodium methanethiolate → 2-(Trifluoromethyl)imidazo[1,2-a]pyridine-6-thiol

HRID 1253823Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[CH:7]=1.C[S-:16].[Na+]>CC(N(C)C)=O>[F:12][C:11]([F:14])([F:13])[C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([SH:16])=[CH:7][N:6]2[CH:8]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine (500 mg, 1.89 mmol) (for the synthesis, see WO2005111047) and sodium thiomethoxide (400 mg, 5.67 mmol) in dimethylacetamide (5 ml) was heated to 150° C. for 90 minutes under a nitrogen atmosphere. The resultant mixture was cooled down to room temperature and partitioned between ethyl acetate and an aqueous solution of ammonium chloride. The aqueous phase was extracted with more ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a red oil (251 mg, 61% yield). MS (ES+) 219, (ES+) 217.

Workup

customfor the synthesis
custompartitioned between ethyl acetate
extractionThe aqueous phase was extracted with more ethyl acetate
washthe combined organic layers were washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c82fd75caa146bfa9f7631c0436e99d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455507B2

Reaction notes

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