Ammonium Chloride → HCID 57763162, compound

HRID 230753Notes

Reaction equation

HRID 230753 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[N:15]=[CH:14][C:13]=3[CH:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[N:15]=[CH:14][C:13]=3[CH:12]=[CH:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 57763159HCID 57763159, compound

Product 1

HCID 57763162HCID 57763162, compoundYield 89.4%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (35 mg, 0.10 mmol), zinc powder (80 mg), and NH4Cl (100 mg) in MeOH (3 mL) and THF (2 mL) was stirred at rt for 15 h. The mixture was diluted with EtOAc, filtered through a pad of Celite®. The filtrate was washed with brine, dried over MgSO4 and concentration in vacuo to afford the title compound as a solid (29 mg, 89%) was obtained. LC-MS: m/z 325 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washThe filtrate was washed with brine
  3. dry with materialdried over MgSO4 and concentration in vacuo

Sources & evidence

ORD record
ord-aa0beb1f11824fb692569cb22792320b
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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