ethyl 7-(azidomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate → ethyl 7-(aminomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854893Notes

Reaction equation

HRID 854893 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][C:6]=1[Cl:24])=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([C:15]([F:17])([F:18])[F:16])[O:12]2)=[CH:7][C:6]=1[Cl:24]

Participants

4

Reactant 1

HCID 86599453ethyl 7-(azidomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69516709ethyl 7-(aminomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 104.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The ester from Step 4 (0.93 g, 2.57 mmole) was dissolved in EtOH (30 mL). 10% Pd-C (0.11 g, 11% weight) was added to the solution after flushing nitrogen. The mixture was stirred at hydrogen sphere for overnight. Pd was filtered off the filtrate was concentrated to give yellow oil (0.9 g, 100%): LCMS m/z 336.05 (M+H). This ester was of suitable purity to use without further purification.

Workup

  1. customafter flushing nitrogen
  2. filtrationPd was filtered off the filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-f797c63d9a6f49acb892902a8e63af10
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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