Dimethylformamide → 2-Bromo-5-[(propan-2-yl)oxy]pyridine

HRID 1645446Notes

Reaction equation

HRID 1645446 reaction equation
Br[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Br:16][C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>C(OCC)(=O)C>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH:2]([CH3:4])[CH3:3])=[CH:21][N:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 547754082-Bromo-5-[(propan-2-yl)oxy]pyridineYield 103%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromopropane (1.13 mL, 12 mmol) and potassium carbonate (1.43 g, 10.4 mmol) were added in that order to a DMF (10 mL) solution of 6-bromopyridin-3-ol (1 g, 5.75 mmol), and stirred at 80° C. for 2 hours. The temperature of the solution was restored to room temperature, then this was diluted with ethyl acetate, washed twice with distilled water and once with saturated brine. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to give the intended product (1.28 g, 100%).

Workup

  1. customwas restored to room temperature
  2. washwashed twice with distilled water and once with saturated brine
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4f7a640570b43d79e31458bf2658636
Source dataset
uspto-grants-2012_02
Patent number
US08124807B2

Reaction notes

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