Potassium Carbonate → 5-(6-Bromopyridin-2-yl)oxazole

HRID 1854591Notes

Reaction equation

HRID 1854591 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC1C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:8]2[O:9][CH:28]=[N:27][CH:26]=2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 583991995-(6-Bromopyridin-2-yl)oxazoleYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-bromopyridine-2-carboxaldehyde (5.90 g, 31.7 mmol) in methanol (150 ml) was added K2CO3 (5.25 g, 38.0 mmol) and TosMIC (7.43 g, 38.0 mmol). After stirring at ambient temperature for 1.5 h, the mixture was concentrated under vacuum and the product precipitated by addition of water. The solid was collected by filtration and dried in a vacuum dessicator at 50° C. to afford 2-bromo-6-oxazol-5-ylpyridine compound as a beige solid (6.81 g, 95% yield). 1H NMR (CDCl3, 300 MHz): δ=7.97 (s, 1H), 7.76 (s, 1H), 7.65-7.57 (m, 2H), 7.48-7.37 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customthe product precipitated by addition of water
  3. filtrationThe solid was collected by filtration
  4. customdried in a vacuum dessicator at 50° C.

Sources & evidence

ORD record
ord-491836f816f6491585c96815b3a50d40
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

Loading…