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

HRID 60228Notes

Reaction equation

HRID 60228 reaction equation
[Cl: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>[Cl: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 583651265-Chloro-3-prop-1-ynyl-pyridin-2-ylamine

Product 1

HCID 199167925-Chloro-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

5-Chloro-3-prop-1-ynyl-pyridin-2-ylamine (53.7 g, 0.32 mol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (515 mL) and the reaction mixture was heated at 85° C. 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 grey solid (44.8 g, 83%). LCMS (Method B): RT=3.64 min, M+H+=167/169. 1H NMR (400 MHz, DMSO-d6): 8.02 (d, J=2.4 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 6.11 (d, J=1.1 Hz, 1H), 2.40 (d, J=1.0 Hz, 3H).

Workup

  1. temperatureto cool to ambient temperature
  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-ea314b0039034e33ad2c0ead7cb3f8a5
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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