Potassium tert-butoxide → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 60212Notes

Reaction equation

HRID 60212 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:9]=[C:10]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 583651355-Bromo-3-prop-1-ynyl-pyridin-2-ylamine

Product 1

HCID 454896915-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 97.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

5-Bromo-3-prop-1-ynyl-pyridin-2-ylamine (91 g, 431 mmol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (700 mL) and the reaction mixture was heated at 85 OC for 1 hour. The mixture was then allowed to cool to ambient temperature and poured onto a 1:1 mixture of water/ice (ca. 1 L). The resultant precipitate was collected by filtration, washed with water and left to air dry. The resultant solid was dissolved in dichloromethane, dried (Na2SO4) and evaporated then triturated with diethyl ether to afford the title compound as a brown solid (88.7 g, 97%). 1H NMR (400 MHz, CDCl3): 10.21 (s, 1H), 8.22 (d, J=2.1 Hz, 1H), 7.91 (d, J=2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated at 85 OC for 1 hour
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with water
  4. waitleft to air
  5. customdry
  6. dissolutionThe resultant solid was dissolved in dichloromethane
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-fe2c3867dd4e4f7993555d645ecad658
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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