Isopropanol → 3-Bromo-5-(propan-2-yloxy)pyridine

HRID 1878619Notes

Reaction equation

HRID 1878619 reaction equation
CN1C(=O)CCC1.[CH3:8][C:9]([O-:12])(C)[CH3:10].[Na+].CC(O)C.Br[C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Br:25])[CH:24]=1>C1(C)C=CC=CC=1>[Br:25][C:23]1[CH:22]=[N:21][CH:20]=[C:19]([O:12][CH:9]([CH3:10])[CH3:8])[CH:24]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 13387N-methyl-2-pyrrolidoneHCID 693693,5-DibromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 105848083-Bromo-5-(propan-2-yloxy)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To NMP (15 eq, 313 mmol, 30.4 ml), NaOtBu (1.5 eq, 31.3 mmol, 3.01 g) is added portion-wise. The mixture is stirred for 1 h at r.t., then 2-propanol (15 eq, 313 mmol, 24 ml) is added over a period of 15 min, followed by the addition of 3,5-dibromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 20.9 mmol, 5.0 g). The resulting mixture is heated at 75° C. for 2 h. After cooling down to r.t., toluene (30 ml) is added and the mixture is washed with water, dried over MgSO4, filtered, and concentrated. Purification of the crude product using column chromatography (hexane/EtOAc) yields the title compound; [M+H]+=217.

Workup

  1. temperatureThe resulting mixture is heated at 75° C. for 2 h
  2. temperatureAfter cooling down to r.t.
  3. washthe mixture is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude product

Sources & evidence

ORD record
ord-16894855686a479bab35066a5f7feb5b
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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