Ammonium Hydroxide → 3-(4-Bromo-1,2-oxazol-3-yl)pyridine

HRID 660182Notes

Reaction equation

HRID 660182 reaction equation
[Br:1][C:2]1[C:3]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:4][O:5][C:6]=1[Si](C)(C)C.[NH4+].[OH-]>CCO>[Br:1][C:2]1[C:3]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:4][O:5][CH:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 575480503-(4-Bromo-5-trimethylsilanyl-isoxazol-3-yl)-pyridine

Product 1

HCID 575480413-(4-Bromo-1,2-oxazol-3-yl)pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of EtOH (20 ml) containing compound 63 (4.5 g, 15.4 mmol) were added 5 ml of 25% NH4OH. After the addition, the resulting solution was stirred for 10 minutes at room temperature. The reaction mixture was concentrated in vacuo. Ethyl acetate was added and the organic layer was washed with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (diethyl ether) afforded the title compound (64) as an oil (2.76 g, 82%). (TLC diethyl ether Rf 0.4). 1H-NMR (400 MHz, CDCl3): δ 9.14 (d, J=2 Hz, 1H), 8.76 (dd, J=5 Hz, 2 Hz, 1H), 8.58 (s, 1H), 8.19 (dt, J=8 Hz, 2 Hz, 1H), 7.48-7.43 (m, 1H).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionEthyl acetate was added
  4. washthe organic layer was washed with a saturated NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (diethyl ether)

Sources & evidence

ORD record
ord-4d3b264faf2e48c9a0fd6de8c8afefa8
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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