Trifluoroacetic acid → HCID 23152428, compound

HRID 1012260Notes

Reaction equation

HRID 1012260 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:14]([CH2:32][CH2:33][CH2:34][Cl:35])[C:15]2[C:20]([C:21]=1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:19][CH:18]=[C:17]([C:28]([O:30][CH3:31])=[O:29])[CH:16]=2)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[Cl:35][CH2:34][CH2:33][CH2:32][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([C:28]([O:30][CH3:31])=[O:29])[CH:16]=2)[C:21]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:13]1[C:9]1[NH:8][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23152316methyl 2-(1-tert-butoxycarbonyl-1H-pyrrol-2-yl)-1-(3-chloropropyl)-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 23152428HCID 23152428, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-(1-tert-butoxycarbonyl-1H-pyrrol-2-yl)-1-(3-chloropropyl)-3-cyclohexyl-1H-indole-6-carboxylate (167 mg, 0.344 mmol) in chloroform (1.5 ml) was added trifluoroacetic acid (1 ml), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was evaporated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give methyl 1-(3-chloropropyl)-3-cyclohexyl-2-(1H-pyrrol-2-yl)-1H-indole-6-carboxylate (135 mg, yield 98%).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-821b721980784f7aad9c3e5fdb28f91a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…