Epibromohydrin → 6-bromo-N-(oxiran-2-ylmethyl)pyridin-2-amine

HRID 1051471Notes

Reaction equation

HRID 1051471 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:12][CH:13]1[CH2:15][O:14]1>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:12][CH:13]2[CH2:15][O:14]2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 867292546-bromo-N-(oxiran-2-ylmethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 6-bromopyridin-2-amine (1 g, 5.81 mmol) in DMF (15 mL) was added NaH (696 mg, 17.4 mmol), 2-(bromomethyl)oxirane (790 mg, 5.81 mmol) at 0° C. The mixture was stirred at 0° C. for 4 hours then quenched with water (50 mL), extracted with EA (30 mL×3). The combined extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was directly for the next step. LCMS (m/z): 279.1/280.1 [M+H]+/[M+2H]+

Workup

  1. customthen quenched with water (50 mL)
  2. extractionextracted with EA (30 mL×3)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bc6ae1092a5947e2be7d2a8a447df1da
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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