Water → HCID 117974191, compound

HRID 2272906Notes

Reaction equation

HRID 2272906 reaction equation
Cl[C:2]1[N:14]([CH3:15])[C:5]2=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]2[N:3]=1.[CH2:16]([S:18][C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17].[H-].[Na+].O>CN(C=O)C>[CH2:16]([S:18][C:19]1[N:20]([C:2]2[N:14]([CH3:15])[C:5]3=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]3[N:3]=2)[CH:21]=[CH:22][CH:23]=1)[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 121622211H-Pyrrole, 2-(ethylthio)-HCID 117974229HCID 117974229, compound

Product 1

HCID 117974191HCID 117974191, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.49 g of 2-chloro-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine in DMF (2 ml) was added to a mixture of 0.24 g of 2-ethylthio-1H-pyrrole, 0.11 g of sodium hydride (60% oil-based) and 3 ml of DMF, and the mixture was stirred at room temperature for 1.5 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesiums sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.53 g of 2-(2-ethylthiopyrrol-1-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (23)).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesiums sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60b3b67c2d7c43c0a308e52c2bb29c02
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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