Ammonium Chloride → HCID 67976246, compound

HRID 706744Notes

Reaction equation

HRID 706744 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1.[NH4+].[Cl-]>CO.[Zn]>[CH3:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[C:9]([NH2:11])[C:10]=3[CH:2]=[N:3]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 67976246HCID 67976246, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (Example 89, Steps A-B; 1.00 g, 2.54 mmol) in MeOH (25 mL) was cooled to 0° C. Zinc dust (0.829 g, 12.7 mmol) was added and the mixture was stirred for 10 minutes. Saturated aqueous NH4Cl was added (25 mL) and the mixture was stirred vigorously for 2 hours at 0° C. and then warmed to ambient temperature and stirred for an additional 2 hours. Additional saturated aqueous NH4Cl was added (12.5 mL) and the mixture was stirred at ambient temperature for an additional 2 hours. The mixture was diluted with MeOH and filtered. To the filtrate was added saturated aqueous NH4OAc and the mixture was concentrated to remove bulk MeOH. The mixture was then extracted with EtOAc and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography (2 to 20% IPA/CHCl3) to afford 0.428 g (70%) of the desired product as an orange solid.

Workup

  1. stirringthe mixture was stirred vigorously for 2 hours at 0° C.
  2. stirringstirred for an additional 2 hours
  3. stirringthe mixture was stirred at ambient temperature for an additional 2 hours
  4. filtrationfiltered
  5. additionTo the filtrate was added saturated aqueous NH4OAc
  6. concentrationthe mixture was concentrated
  7. customto remove bulk MeOH
  8. extractionThe mixture was then extracted with EtOAc
  9. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude material was purified by column chromatography (2 to 20% IPA/CHCl3)

Sources & evidence

ORD record
ord-fccf0ba04d18417eb8bbf9679cfc36ec
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…