Methanol → HCID 67004992, compound

HRID 1513983Notes

Reaction equation

HRID 1513983 reaction equation
C([O:8][C:9]1[CH:43]=[CH:42][C:12]2[C:13]3[CH:14]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]5[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]5)=[CH:29][CH:28]=4)[N:15]([CH3:26])[C:16]4[CH:17]=[C:18]([F:25])[CH:19]=[CH:20][C:21]=4[C:22]=3[CH:23]=[CH:24][C:11]=2[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>[Pd].C(O)C>[F:25][C:18]1[CH:19]=[CH:20][C:21]2[C:22]3[CH:23]=[CH:24][C:11]4[CH:10]=[C:9]([OH:8])[CH:43]=[CH:42][C:12]=4[C:13]=3[CH:14]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:31][CH:32]=3)[N:15]([CH3:26])[C:16]=2[CH:17]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 11296083HCID 11296083, compound

Product 1

HCID 67004992HCID 67004992, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask add 2-benzyloxy-8-fluoro-6-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,6-dihydro-benzo[i]phenanthridine (0.030 g, 0.052 mmol), ammonium formate (0.026 g, 0.42 mmol), methanol (5 mL) and a slurry of 10% Pd/C (0.005 g, ˜15% by weight) and ethanol (2 mL). Heat the mixture, with stirring, at reflux for 30 minutes. Cool the reaction to ambient temperature and filter it through a pad of Celite, then rinse the Celite with hot methanol. Evaporate the filtrate in vacuo and purify the resulting residue by radial chromatography over silica (5-10% MeOH gradient in CH2Cl2) to provide the product 20 mg (80%); mass spectrum (ion spray) m/z=483 (M+H).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 30 minutes
  3. temperatureCool
  4. customthe reaction to ambient temperature
  5. filtrationfilter it through a pad of Celite
  6. washrinse the Celite with hot methanol
  7. customEvaporate the filtrate in vacuo
  8. custompurify the resulting residue by radial chromatography over silica (5-10% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-6c115ff3b5d54562aee5692227b61bc1
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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