Ammonium formate → HCID 22611211, compound

HRID 726387Notes

Reaction equation

HRID 726387 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:13][C:12]2=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH:22][CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH2:13][C:12]2=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22611580HCID 22611580, compound

Product 1

HCID 22611211HCID 22611211, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.700 gm (1.69 mMol) 6-benzyloxy-3-(2-(4-fluorophenyl)eth-1-yl)amino-1,2,3,4-tetrahydro-9H-carbazole in 50 mL methanol were added 1.07 gm (16.90 mMol) ammonium formate followed by 0.190 gm 5% palladium on carbon. The resulting mixture was stirred at reflux for 15 minutes. The reaction mixture was then filtered through a bed of celite and the filter cake washed well with methanol. The combined filtrates were concentrated under reduced pressure and the residue partitioned between water and dichloromethane. The phases were separated and the aqueous was extracted again with 4:1 isopropanol:dichloromethane. The combined extracts were dried over magnesium sulfate, concentrated under reduced pressure, and the residue subjected to silica gel chromatography, eluting with 91:8:1 dichloromethane:methanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.245 gm (52%) of 6-hydroxy-3-(2-(4-fluorophenyl)eth-1-yl)amino-1,2,3,4-tetrahydro-9H-carbazole. The hydrochloride salt was prepared and crystallized from ethanol/diethyl ether to give the title compound.

Workup

  1. temperatureat reflux for 15 minutes
  2. filtrationThe reaction mixture was then filtered through a bed of celite
  3. washthe filter cake washed well with methanol
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customthe residue partitioned between water and dichloromethane
  6. customThe phases were separated
  7. extractionthe aqueous was extracted again with 4:1 isopropanol
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washeluting with 91:8:1 dichloromethane
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1769af9675640f0bf8a33cf0280523d
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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