Methyl iodide → (6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-methyl-carbamic acid tert-butyl ester

HRID 347689Notes

Reaction equation

HRID 347689 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[N:10][C:11]([Cl:21])=[CH:12][C:13]=1[C:14]1[C:15]([CH3:20])=[N:16][CH:17]=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[N:7]([C:8]1[CH:9]=[N:10][C:11]([Cl:21])=[CH:12][C:13]=1[C:14]1[C:15]([CH3:20])=[N:16][CH:17]=[CH:18][CH:19]=1)[CH3:25])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58694598(6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl ester

Product 1

HCID 58694607(6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-methyl-carbamic acid tert-butyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.16 g (0.50 mmol) (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-carbamic acid tert-butyl ester in 5 ml DMF were added 25 mg (0.50 mmol) sodium hydride (50% suspension in mineral oil) under nitrogen at room temperature. After stirring for 30 min 0.034 ml (0.52 mmol) methyl iodide were added. The reaction mixture was stirred for 1 h. Quenching with water was followed by extraction with three portions of dichloromethane. The combined organic layers were washed with water. The combined aqueous layers were extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and concentrated. Residual DMF was removed by Kugelrohr distillation. Flash chromatography gave 0.14 g (84%) of the title compound.

Workup

  1. additionwere added
  2. customQuenching with water
  3. extractionwas followed by extraction with three portions of dichloromethane
  4. washThe combined organic layers were washed with water
  5. extractionThe combined aqueous layers were extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. concentrationconcentrated
  8. customResidual DMF was removed by Kugelrohr distillation

Sources & evidence

ORD record
ord-3477e95c22354478ba25ebd5b4ea1254
Source dataset
uspto-grants-2007_02
Patent number
US07176205B2

Reaction notes

Loading…