Trifluoroacetic acid → HCID 9861834, compound

HRID 22788Notes

Reaction equation

HRID 22788 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:24]=[CH:23][C:22]2[NH:21][CH:20]3[CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][CH:19]3[C:18]=2[CH:17]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:24]=[CH:23][C:22]2[NH:21][CH:20]3[CH2:25][CH2:26][NH:27][CH2:28][CH:19]3[C:18]=2[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22591897HCID 22591897, compound

Product 1

HCID 9861834HCID 9861834, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml flask, tert-butyl 8-(2,4-dichlorophenyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (215 mg) was dissolved in 5 mL dichloromethane and cooled to 0° C. with an ice bath. After the addition of 5 mL trifluoroacetic acid, the reaction stirred at room temperature for 45 minutes. The reaction was concentrated in vacuo then diluted with 5M sodium hydroxide. After three ethyl acetate extractions, the combined organics were washed with brine then dried over magnesium sulfate and concentrated to give crude material which was purified by column chromatography (0.5/5/93.5 ammonium hydroxide/methanol/dichloromethane) to give 101 mg (62%) of the title compound as an off-white solid. MS (ESI+) for C17H16N2Cl2 m/z 319.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthen diluted with 5M sodium hydroxide
  3. extractionAfter three ethyl acetate extractions
  4. washthe combined organics were washed with brine
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give crude material which
  8. customwas purified by column chromatography (0.5/5/93.5 ammonium hydroxide/methanol/dichloromethane)

Sources & evidence

ORD record
ord-905ad1caeef14580869183ec8db13079
Source dataset
uspto-grants-2005_02
Patent number
US06849640B2

Reaction notes

Loading…