Methyl iodide → 2-(N-BOC-N-methylamino)-5-bromopyridine

HRID 1692762Notes

Reaction equation

HRID 1692762 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[C:16](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 162178432-(Boc-amino)-5-bromopyridine

Product 1

HCID 111969422-(N-BOC-N-methylamino)-5-bromopyridineYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl 5-bromopyridin-2-ylcarbamate (10 g) and cesium carbonate (20 g) were added to 50 mL of DMF. Methyl iodide (4 mL) was subsequently slowly added to the stirring reaction mixture. After 30 minutes tlc indicates that the reaction is complete. The majority of the DMF was removed under hi-vacuum and the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried, filtered and concentrated. The crude product was purified by Isco 0-30% gradient (WE) over 25 mins. The tubes were pooled and concentrated to get 9.85 g of tert-butyl 5-bromopyridin-2-yl(methyl)carbamate as a clear oil.

Workup

  1. customThe majority of the DMF was removed under hi-vacuum
  2. extractionthe reaction mixture was extracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by Isco 0-30% gradient (WE) over 25 mins
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6f258aaf78414270b2971a3b76699ad4
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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