Dimethylformamide → [2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

HRID 734873Notes

Reaction equation

HRID 734873 reaction equation
[H-].[Na+].[Br:3][C:4]1C(N)=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:6][N:5]=1.CI.[CH3:20][N:21]([CH:23]=O)[CH3:22]>C(=O)(O)[O-].[Na+]>[Br:3][C:4]1[C:23]([N:21]([CH3:22])[CH3:20])=[CH:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 85969704HCID 85969704, compound

Product 1

HCID 86076948[2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

169 mg (3.88 mmol) of sodium hydride (55% suspension) was added batchwise under a nitrogen atmosphere to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 10 mL of DMF and the mixture was stirred for 15 minutes at RT. A solution of 0.22 mL (3.53 mmol) of methyl iodide in 0.5 mL of DMF was added and the mixture was stirred for 16 hours at RT. The reaction mixture was diluted with semisaturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.47 g (85% of theoretical); C13H12BrClN2 (M=311.605); calc.: molpeak (M+H)+: 311/313/315 (BrCl); found: molpeak(M+H)+:311/313/315 (BrCl).

Workup

  1. stirringthe mixture was stirred for 16 hours at RT
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo

Sources & evidence

ORD record
ord-4f2cf573d2a24d8880af039e1cb73627
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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