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

HRID 60220Notes

Reaction equation

HRID 60220 reaction equation
[F: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>[F: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 583652185-Fluoro-3-prop-1-ynyl-pyridin-2-ylamine

Product 1

HCID 199167765-Fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

5-Fluoro-3-prop-1-ynyl-pyridin-2-ylamine (14.0 g, 90.0 mmol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (150 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), filtered and evaporated then triturated with diethyl ether to afford the title compound as a buff solid (9.2 g, 66%). 1H NMR (300 MHz, CDCl3): 10.61 (s, 1H), 8.12 (s, 1H), 7.51 (dd, J=9.1, 2.3 Hz, 1H), 6.17 (s, 1H), 2.53 (d, J=1.0 Hz, 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. filtrationfiltered
  9. customevaporated
  10. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-35fd77f50dc0410fa53ebb76696ec907
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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