Ammonium Chloride → HCID 67259271, compound

HRID 79312Notes

Reaction equation

HRID 79312 reaction equation
[I:1][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:16]=[N:17][N:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH:19]=2)[N:3]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[I:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH2:14][C:15]2[CH:16]=[N:17][N:18]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[CH:19]=2)[N:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 672616463-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 67259271HCID 67259271, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 3-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-4-nitro-1H-indazole (1.13 g, 2.31 mmol) in EtOH/H2O (20 mL/5 mL) was added iron (1.29 g, 23.1 mmol) and NH4Cl (0.124 g, 2.31 mmol). The reaction mixture was heated to 80° C. and stirred for 3 hours. The reaction mixture was concentrated, diluted with EtOAc (30 mL) and Et3N (5 mL). The reaction mixture was heated to reflux for 30 minutes and filtered through Celite®, and the filter pad was washed with DCM/MeOH (50 mL, 10:1). The filtrate was concentrated to provide the desired product (0.89 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (30 mL) and Et3N (5 mL)
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 30 minutes
  5. filtrationfiltered through Celite®
  6. washthe filter pad was washed with DCM/MeOH (50 mL, 10:1)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5bc87513b3f74fd19e456e712d38c485
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…