Ammonium formate → HCID 59129351, compound

HRID 1847836Notes

Reaction equation

HRID 1847836 reaction equation
[CH3:1][C:2]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][CH:16]=2)([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O-])=O.[NH4+]>C1COCC1.O.[Pd]>[NH2:22][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:2]([CH3:12])([CH3:1])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[CH:21]2

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 59129535HCID 59129535, compound

Product 1

HCID 59129351HCID 59129351, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propylcarbamate (80 mg, 0.24 mmol) in THF (9 mL) and water (2 mL) was added ammonium formate (60 mg, 0.96 mmol) followed by 10% Pd/C (50 mg). The mixture was stirred at room temperature for 45 minutes. Pd/C was filtered off and the organic solvent was removed by evaporation. The remaining aqueous phase was extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate and evaporated to give tert-butyl 2-(5-amino-1H-indol-2-yl)-2-methylpropylcarbamate (58 mg, 80%).

Workup

  1. filtrationPd/C was filtered off
  2. customthe organic solvent was removed by evaporation
  3. extractionThe remaining aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-5f3a881c351e428ca9d9f546ce97bc47
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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