Allyl bromide → HCID 21849063, compound

HRID 1057489Notes

Reaction equation

HRID 1057489 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([Li])[CH2:17][CH2:18]C.C(Br)C=C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:18][CH:17]=[CH2:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 21849063HCID 21849063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirring solution of (tert-butoxy)-N-(6-methyl(2-pyridyl))carboxamide in tetrahydrofuran (0.1 M) was added n-butyl lithium (2.1 eq) at −78° C. and the solution was warmed to 25° C. and stirred for 1 hr. The solution was then cooled back down to −78° C. followed by addition of allyl bromide (1.5 eq) and continued strirring for 1 hr. The reaction was quenched with saturated ammonium chloride, diluted with ethyl acetate and separated. The organic layer was washed with brine and dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (5% EtOAc/Hexane). EI-MS m/z 249(M+H)+

Workup

  1. temperatureThe solution was then cooled back down to −78° C.
  2. waitcontinued strirring for 1 hr
  3. customThe reaction was quenched with saturated ammonium chloride
  4. additiondiluted with ethyl acetate
  5. customseparated
  6. washThe organic layer was washed with brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-00f8e7e51ba242e1bbd2a2198df08ea3
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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