Ammonium Chloride → 2-(5-Amino-6-trifluoromethyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

HRID 1180592Notes

Reaction equation

HRID 1180592 reaction equation
[CH2:1]([S:3][CH2:4][C:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-])=O)=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)([OH:7])[CH3:6])[CH3:2].[Cl-].[NH4+].[In]>C(O)C.ClCCl>[NH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[C:20]([F:23])([F:21])[F:22])[NH:9][C:8]([C:5]([OH:7])([CH3:6])[CH2:4][S:3][CH2:1][CH3:2])=[CH:16]2

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 444311401-ethylsulfanyl-2-(5-nitro-6-trifluoromethyl-1H-indol-2-yl)-propan-2-ol

Product 1

HCID 115948662-(5-Amino-6-trifluoromethyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-ethylsulfanyl-2-(5-nitro-6-trifluoromethyl-1H-indol-2-yl)-propan-2-ol (0.35 g, 1.0 mmol) in ethanol. (20 mL) was prepared. To the solution was then added saturated ammonium chloride solution (20 mL). Indium was added (1.15 g, 10 mmol) and the reaction heated to reflux. After one-half hour the reaction was complete. The reaction mixture was filtered through Celite and the Celite washed with water and diethyl ether. The layers were separated and the aqueous layer extracted with diethyl ether. The organic layers were dried over magnesium sulfate, filtered, and evaporated to yield a residue. The residue was dissolved in dichloromethane and purified by column chromatography eluting with 1:1 diethyl ether/hexanes to yield the title compound as a solid.

Workup

  1. custom(20 mL) was prepared
  2. temperaturethe reaction heated to reflux
  3. waitAfter one-half hour the reaction was complete
  4. filtrationThe reaction mixture was filtered through Celite
  5. washthe Celite washed with water and diethyl ether
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with diethyl ether
  8. dry with materialThe organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto yield a residue
  12. custompurified by column chromatography
  13. washeluting with 1:1 diethyl ether/hexanes

Sources & evidence

ORD record
ord-bed42f024ec847d7a86c44ea1ef4c67f
Source dataset
uspto-grants-2007_10
Patent number
US07282507B2

Reaction notes

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