Sodium Hydroxide → HCID 68091199, compound

HRID 923773Notes

Reaction equation

HRID 923773 reaction equation
Cl[CH:2]([C:7]1[CH:8]=[C:9]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[S:22][CH2:23][CH3:24])[N:13]([CH3:25])[C:10]2=[N:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4].[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:23]([S:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:13]([CH3:25])[C:10]2=[N:11][CH:12]=[C:7]([CH2:2][C:3]([F:5])([F:6])[F:4])[CH:8]=[C:9]2[N:15]=1)[CH3:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 68091097HCID 68091097, compound

Product 1

HCID 68091199HCID 68091199, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6-(1-chloro-2,2,2-trifluoro-ethyl)-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (61 mg) and methanol (5 ml), sodium borohydride (20 mg) was added under ice-cooling. The mixture was stirred at room temperature for 3 hours, and then 1N aqueous sodium hydroxide solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 40 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-(2,2,2-trifluoro-ethyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 165).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2b5590c47274fea883ef4815f6c4846
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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