Potassium Carbonate → Ethyl 5-((tert-butoxycarbonyl)amino)-4-fluoropyrazolo[1,5-a]pyridine-3-carboxylate

HRID 926741Notes

Reaction equation

HRID 926741 reaction equation
C([O-])([O-])=O.[K+].[K+].[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:20][N+:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:23]([F:35])[CH:22]=1.[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[C:37]#[CH:38]>C1COCC1>[C:31]([O:30][C:28]([NH:27][C:24]1[CH:25]=[CH:26][N:21]2[N:20]=[CH:38][C:37]([C:36]([O:40][CH2:41][CH3:42])=[O:39])=[C:22]2[C:23]=1[F:35])=[O:29])([CH3:32])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12182Ethyl propiolateHCID 896190191-Amino-4-((tert-butoxycarbonyl)amino)-3-fluoropyridin-1-ium 2,4-dinitrophenolate

Product 1

HCID 89618648Ethyl 5-((tert-butoxycarbonyl)amino)-4-fluoropyrazolo[1,5-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

K2CO3 (36.96 g, 267 mmol) was added to a solution of 1-amino-4-((tert-butoxycarbonyl)amino)-3-fluoropyridin-1-ium 2,4-dinitrophenolate (50 g, 121 mmol) in THF (500 mL) at 28° C. and continued stirring at same temperature for 30 min. Ethyl propiolate (14.3 g, 145 mmol) was added to above solution and stirring was continued at 28° C. for 16 hr. Reaction mixture was filtered to remove the salt, filtrate collected was diluted with EtOAc washed it with water followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude. The crude obtained was purified by column purification (using 60-120 silicagel and 10% EtOAc in Hexane as eluant) to afford the title compound MS m/z 323.9 (M+H)

Workup

  1. stirringstirring
  2. waitwas continued at 28° C. for 16 hr
  3. customReaction mixture
  4. filtrationwas filtered
  5. customto remove the salt, filtrate
  6. customcollected
  7. additionwas diluted with EtOAc
  8. washwashed it with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customto afford crude
  12. customThe crude obtained
  13. customwas purified by column purification (using 60-120 silicagel and 10% EtOAc in Hexane as eluant)

Sources & evidence

ORD record
ord-0d7fab78a44741529c047fbe90fb113b
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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