tert-Butanol → 3,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

HRID 493144Notes

Reaction equation

HRID 493144 reaction equation
[Br:1]Br.[Br:3][C:4]1([Br:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].CC(O)(C)C>O>[Br:14][C:4]1([Br:3])[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Br:1])[CH:11]=2)[NH:6][C:5]1=[O:13]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24408BromineHCID 138640943,3-Dibromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Product 1

HCID 219561923,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Bromine (13.4 mL, 0.262 mol) was added dropwise over a period of 30 min to a cooled (ice bath) and stirred suspension of 2 (37.86 g, 0.131 mol) in water:t-BuOH=1:1 (1500 mL). Cooling bath was removed and the mixture was stirred at r.t. overnight. Then the solution was cooled to 15° C. and saturated aqueous solution of NaHCO3 (278 mL) was added. A yellow suspension, which was formed, was concentrated in vacuum (bath temperature <32° C.) until about 1000 mL of condensate was collected. The solid was filtered off, washed with water (200 mL), and dried in vacuum to afford 3 (40.85 g, 85%) as tan powder.

Workup

  1. temperaturea cooled (ice bath)
  2. temperatureCooling bath
  3. customwas removed
  4. stirringthe mixture was stirred at r.t. overnight
  5. additionsaturated aqueous solution of NaHCO3 (278 mL) was added
  6. customA yellow suspension, which was formed
  7. concentrationwas concentrated in vacuum (bath temperature <32° C.) until about 1000 mL of condensate
  8. customwas collected
  9. filtrationThe solid was filtered off
  10. washwashed with water (200 mL)
  11. customdried in vacuum

Sources & evidence

ORD record
ord-1dcb0246506b4d4ab4d798514a951743
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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