Ammonium → HCID 117974188, compound

HRID 2272900Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[N:19]([CH3:20])[C:10]2=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=[C:9]2[N:8]=1.[Na].[CH2:22]([SH:24])[CH3:23].CN1CCCC1=O.[NH4+]>[Cu](I)I.O>[CH2:22]([S:24][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[N:19]([CH3:20])[C:10]2=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=[C:9]2[N:8]=1)[CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 0.72 g of 2-(2-bromothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine, 0.25 g of ethyl mercaptan sodium salt (80%), 0.08 g of copper iodide and 4 ml of N-methylpyrrolidinone was stirred at 70° C. for 4 hours. Water and aqueous ammonium (28%) were poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.30 g of 2-(2-ethylthiothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (13)).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f74e72c736fe43289fe86d2c8a838b3d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120792B2

Reaction notes

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