N-bromobutanimide → 4-Benzyloxy-3-bromo-1-cyclopropylmethyl-1H-pyridin-2-one

HRID 516629Notes

Reaction equation

HRID 516629 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:11](=[O:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH:16]2[CH2:17][CH2:18]2)[C:11](=[O:19])[C:10]=1[Br:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 594970994-(Benzyloxy)-1-(cyclopropylmethyl)pyridin-2(1H)-one

Product 1

HCID 594970894-Benzyloxy-3-bromo-1-cyclopropylmethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of intermediate D1 (3.0 g, 11.7 mmol) and N-bromosuccinimide (2.09 g, 11.7 mmol) in DCM (100 ml) was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo and the crude residue was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo yielding D33 (3.56 g, 91%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude residue was purified by column chromatography (silica gel; DCM as eluent)
  3. customThe desired fractions were collected
  4. customevaporated in vacuo
  5. customyielding D33 (3.56 g, 91%)

Sources & evidence

ORD record
ord-3d5ce9cab12941d29abefe9e5b0461db
Source dataset
uspto-grants-2015_08
Patent number
US09114138B2

Reaction notes

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