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

HRID 1027555Notes

Reaction equation

HRID 1027555 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 vauo. 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 vauo
  9. customPurification by flash chromatography (diethyl ether)

Sources & evidence

ORD record
ord-7d47b6e4d68a4dc09b5e8251e67aff9b
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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