Sodium hydride → HCID 21914466, compound

HRID 533928Notes

Reaction equation

HRID 533928 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([SH:8])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:12][CH:13]1[CH2:15][CH2:14]1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178527717HCID 178527717, compound

Product 1

HCID 21914466HCID 21914466, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromopyridine-2-thiol (3.9 g) in THF (100 mL) was added NaH (1.24 g) at 0° C. and the mixture was stirred at 0° C. for 0.5 h. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to r.t. and stirred for 6 hours. The mixture was poured into ice water (200 mL) and extracted with EA (100 mL×3). The combined organic phases were washed with brine (50 mL) and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI+: m/z=244 [M+H]+.

Workup

  1. temperatureto warm to r.t.
  2. stirringstirred for 6 hours
  3. extractionextracted with EA (100 mL×3)
  4. washThe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of the solvent
  7. customthe residue was purified by SGC (eluent: PE)

Sources & evidence

ORD record
ord-72ef5daf47d649678eab439e7c4e3bbe
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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