Bromine → 3-(4-Bromo-5-trimethylsilanyl-isoxazol-3-yl)-pyridine

HRID 660181Notes

Reaction equation

HRID 660181 reaction equation
C[Si](C)(C)[C:3]1[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:5][O:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9].[Br:20]Br>C(Cl)(Cl)(Cl)Cl>[Br:20][C:3]1[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:5][O:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 575480363-(4,5-Bis-trimethylsilanyl-isoxazol-3-yl)-pyridine

Product 1

HCID 575480503-(4-Bromo-5-trimethylsilanyl-isoxazol-3-yl)-pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of anhydrous CCl4 (80 ml) containing compound 62 (4.45 g, 15.4 mmol) was added (1.1 eq, 1.04 ml) Br2. After the addition, the resulting solution was stirred for 18 hours at 40° C. The reaction mixture was cooled and 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 3-(4-bromo-5-trimethylsilanyl-isoxazol-3-yl)-pyridine (63) as an oil (4.5 g, ˜100%). 1H-NMR (400 MHz, CDCl3) δ 9.08 (d, J=2 Hz, 1H), 8.73 (dd, J=5 Hz, 2 Hz, 1H), 8.14 (dt, J=8 Hz, 2 Hz, 1H), 7.46-7.41 (m, 1H), 0.40 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-4d2d2d24ce3846348126769320ac5522
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

Loading…