Dimethylformamide → HCID 117974266, compound

HRID 2272902Notes

Reaction equation

HRID 2272902 reaction equation
Cl[C:2]1[CH:6]=[CH:5][S:4][C:3]=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.Br[C:22]1C=C[S:24][C:23]=1C1N(C)C2=NC=C(C(F)(F)F)C=C2N=1.[Na].C(S)C.CN(C=O)C>O>[CH2:23]([S:24][C:2]1[CH:6]=[CH:5][S:4][C:3]=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)[CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 45051917Sodium ethanethiolHCID 117974059HCID 117974059, compoundHCID 117974601HCID 117974601, compound

Product 1

HCID 117974266HCID 117974266, compoundYield 188%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.22 g of 2-(3-chlorothiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine, 0.23 g of 2-(3-bromothiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine, 0.21 g of ethyl mercaptan sodium salt (80%) and 4 ml of DMF was stirred at 100° C. for 30 minutes. Water was 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 0.41 g of 2-(3-ethylthiothiophen-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (15)).

Workup

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

Sources & evidence

ORD record
ord-879b455beebb41b2a52f52c758f3c692
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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