Hydrazine → 3-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

HRID 2261619Notes

Reaction equation

HRID 2261619 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][CH:18]([C:22](=O)[CH3:23])[C:19](=O)[CH3:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][NH2:26]>CO.ClCCl>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][C:18]2[C:22]([CH3:23])=[N:25][NH:26][C:19]=2[CH3:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 59593276HCID 59593276, compound

Product 1

HCID 595933443-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(2-acetyl-3-oxo-butyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (513, 1.20 g, 3.63 mmol) in methanol (15.0 mL), cooled to −20° C. under an atmosphere of nitrogen, was added hydrazine (0.128 g, 4.00 mmol) in dichloromethane (6.0 mL). The reaction was stirred for 2 hours. The reaction was concentrated to remove the solvents, and the residue was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 60% ethyl acetate in hexane to give a white solid (514, 1.0 g, 84.4%). MS (ESI) [M+H+]+=327.4.

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove the solvents
  3. additionthe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography
  9. washeluting with 60% ethyl acetate in hexane
  10. customto give a white solid (514, 1.0 g, 84.4%)

Sources & evidence

ORD record
ord-f4ffe05788a94c43a990e12ef3c16073
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

Loading…