1-Propanol → 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl ester

HRID 217955Notes

Reaction equation

HRID 217955 reaction equation
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:8]2[C:7]([C:17]#N)=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=[O:26])=CC=1.[CH2:30]([OH:33])[CH2:31][CH3:32]>COC(C)(C)C>[CH2:30]([O:33][C:17]([C:7]1[C:8]2[C:9](=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1)=[O:26])[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 6101p-Toluenesulfonic acidHCID 669245201H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(1,1-dimethylethyl)-5-nitro-

Product 1

HCID 669245181H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a suspension of 5.0 g (20.47 mmol) of 1-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile in 125 mL of n-propanol, 7.78 g of p-toluensulfonic acid were added under stirring. The mixture was heated at reflux for 40 hours and then it was cooled to room temperature and diluted with 70 mL of tert-butyl methyl ether. The precipitate was filtered off and the clear filtrate was concentrated under vacuum to a small volume (about 40-50 mL). The suspension was cooled to −5/0° C. and kept at this temperature for 2 hours. The solid was filtered, washed with 20 mL of 1:1 mixture of n-propanol and tert-butyl methyl ether and dried to afford 5.50 g of the title compound as a cream-colored solid.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 40 hours
  4. filtrationThe precipitate was filtered off
  5. concentrationthe clear filtrate was concentrated under vacuum to a small volume (about 40-50 mL)
  6. temperatureThe suspension was cooled to −5/0° C.
  7. filtrationThe solid was filtered
  8. washwashed with 20 mL of 1:1 mixture of n-propanol and tert-butyl methyl ether
  9. customdried

Sources & evidence

ORD record
ord-668c62337f25451aae9f96859c6d4982
Source dataset
uspto-grants-2012_06
Patent number
US08198298B2

Reaction notes

Loading…