[9-(6-Fluoro-pyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-carbamic acid benzyl ester → 9-(6-Fluoropyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine

HRID 545544Notes

Reaction equation

HRID 545544 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][C:25]([F:28])([F:27])[F:26])[CH:20]=3)[N:15]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[N:31]=3)[C:14]=2[CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>CCO.C1COCC1.[Pd]>[F:36][C:32]1[N:31]=[C:30]([CH2:29][N:15]2[C:14]3[CH2:13][CH2:12][CH:11]([NH2:10])[CH2:23][C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[C:19]([O:24][C:25]([F:28])([F:26])[F:27])[CH:20]=3)[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 59161299[9-(6-Fluoro-pyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-carbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 574316659-(6-Fluoropyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-ylamineYield 117.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [9-(6-fluoro-pyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-carbamic acid benzyl ester (Preparation 45) (2.73 g, 5.32. mmol) in EtOH (100 mL) and THF (50 mL). Add 10% Pd/C (200 mg) and stir at room temperature under a balloon of hydrogen for 18 h. Filter the reaction through a pad of Celite®, rinse the pad with THF (50 mL), and concentrate the filtrate in vacuo to afford 2.37 g (90%) of the title compound as a dark brown oil. MS (ES): m/z 380 (M+1); HPLC (Method A): Rt=1.76 min (89%).

Workup

  1. filtrationFilter
  2. customthe reaction through a pad of Celite®
  3. washrinse the pad with THF (50 mL)
  4. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-2cb7b05686ea42518552f7f1906a9397
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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