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

HRID 1931309Notes

Reaction equation

HRID 1931309 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]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromopropane (1.13 mL, 12 mmol) and potassium carbonate (1.43 g, 10.4 mmol) were successively added to a DMF (10 mL) solution of 6-bromopyridin-3-ol (1 g, 5.75 mmol), and the mixture was stirred at 80 degrees for 2 hours. The solution was brought back to room temperature, diluted with ethyl acetate, and washed twice with distilled water, and once with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain the target (1.28 g, 100%).

Workup

  1. customwas brought back to room temperature
  2. washwashed twice with distilled water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the target (1.28 g, 100%)

Sources & evidence

ORD record
ord-8e7b82124df540a7a916f94a229344eb
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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