2-Bromopropane → 5-Bromo-1-isopropylpyridin-2(1H)-one

HRID 869035Notes

Reaction equation

HRID 869035 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].BrC(C)C>COCCOC>[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH:2]([CH3:3])[CH3:1])[CH:13]=1

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 5995285-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 467388205-Bromo-1-isopropylpyridin-2(1H)-oneYield 62.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium tert-butoxide (16.80 g, 18.63 mL, 142.2 mmol) was added to a suspension of 5-bromo-1H-pyridin-2-one (25 g, 142.2 mmol) in DME (247.5 mL) and the mixture stirred at ambient temperature for 30 minutes. To the mixture was added potassium carbonate (13.76 g, 99.54 mmol) and 2-bromopropane (34.98 g, 26.70 mL, 284.4 mmol) and the reaction mixture heated at reflux for 64 hours. The reaction mixture was filtered to remove the resultant precipitate and the filtrate concentrated in vacuo. The residue was recrystalised from DCM/hexane to give the sub-title product as an off-white solid (19.1 g 62% Yield). 1H NMR (400.0 MHz, CDCl3) δ 1.36 (d, 6H), 5.22 (dt, 1H), 6.49 (d, 1H), 7.31 (dd, 1H) and 7.41 (d, 1H) ppm; MS (ES+) 217.3.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 64 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove the resultant precipitate
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was recrystalised from DCM/hexane

Sources & evidence

ORD record
ord-4c55c5b1f71c4dbcb2d66d0438412630
Source dataset
uspto-grants-2015_03
Patent number
US08969356B2

Reaction notes

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