4-Bromo-2-methylbenzonitrile → HCID 59186105, compound

HRID 923108Notes

Reaction equation

HRID 923108 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:10][C:4]1[CH:3]=[C:2]([S:12][CH3:11])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 1442674-Bromo-2-methylbenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 59186105HCID 59186105, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg of 4-bromo-2-methylbenzonitrile and 268 mg of sodium thiomethoxide in 3 mL of DMF was stirred for 1 h. The reaction mixture was diluted with ethyl acetate, washed with H2O, dried (MgSO4) and evaporated to afford 2-methyl-4-(methylthio)benzonitrile. 400 mg of 2-methyl-4-(methylthio)benzonitrile was reacted via Procedure T to give 2-methyl-4-(methylthio)benzoic acid. 430 mg of 2-methyl-4-(methylthio)benzoic acid was reacted via Procedure R to yield 2-methyl-4-(methylsulfonyl)benzoic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-methyl-4-(methylsulfonyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-4-(methylsulfonyl)benzamide. MS (Q1) 401.0 (M)+.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-5152d7aadd524e88b98b6574f9048360
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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