Ethyl Acetate → 4-(2-Trifluoromethyl-5,6,7,8-tetrahydro-indolizin-3-yl)phenylamine

HRID 38808Notes

Reaction equation

HRID 38808 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]3[C:13]([CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])=[CH:6][CH:5]=1)([O-])=O.CCOC(C)=O>CO.[Pd]>[F:22][C:19]([F:20])([F:21])[C:11]1[CH:12]=[C:13]2[N:18]([C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH2:17][CH2:16][CH2:15][CH2:14]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59296676HCID 59296676, compound

Product 1

HCID 592967164-(2-Trifluoromethyl-5,6,7,8-tetrahydro-indolizin-3-yl)phenylamineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 400 mg (1.3 mmol) of 3-(4-Nitro-phenyl)-2-trifluoromethyl-indolizine in 12 mL MeOH was added 200 mg (10%) Pd/C. The solution was allowed to stir under a H2 atmosphere for 24 hrs then filtered through celite and concentrated in vacuo. The resulting oil was purified by silica gel chromatography Hexane:EtOAc (gradient 9:1-1:1) to yield 300 mg (1.1 mmol, 85%) of 4-(2-Trifluoromethyl-5,6,7,8-tetrahydro-indolizin-3-yl)-phenylamine.

Workup

  1. filtrationthen filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified by silica gel chromatography Hexane

Sources & evidence

ORD record
ord-64891fc1e7104030b7278565e321a73a
Source dataset
uspto-grants-2013_09
Patent number
US08524756B2

Reaction notes

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