Hydrochloric Acid → HCID 178481757, compound

HRID 1627988Notes

Reaction equation

HRID 1627988 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[CH3:13][NH:14][NH2:15].Cl.O>CCCCO>[CH3:13][N:14]1[C:2]2=[C:3]3[CH:12]=[CH:11][NH:10][C:4]3=[N:5][CH:6]=[C:7]2[CH:8]=[N:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6061MethylhydrazineHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 178481757HCID 178481757, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.37 g, 7.59 mmol) and methylhydrazine (0.59 mL, 11.4 mmol) in n-BuOH (7 mL) was heated to 95° C. After 15 min, aqueous 38% HCl (0.55 mL, 8.83 mmol) was added and the mixture was heated to 120° C. After 4 h, water (10 mL) was added to the mixture and extracted with EtOAc (20 mL). The aqueous layer was separated and basified with saturated aqueous NaHCO3 to pH of 8 and extracted with EtOAc (2×20 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified via flash chromatography with a gradient of 5 to 60% EtOAc/heptane to give 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.960 g, 73%): LC/MS (Table 2, Method b) Rt=1.49 min; MS m/z 173 (M+H)+.

Workup

  1. waitAfter 4 h
  2. extractionextracted with EtOAc (20 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash chromatography with a gradient of 5 to 60% EtOAc/heptane

Sources & evidence

ORD record
ord-ef90ecf852f944d29e27eb8fcc928726
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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