Trifluoroacetic acid → HCID 86627576, compound

HRID 1970070Notes

Reaction equation

HRID 1970070 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]3[CH:33]=[CH:32][C:31]4[NH:30][C:29](=[O:34])[C:28]5[NH:35][CH:36]=[CH:37][C:27]=5[C:26]=4[CH:25]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=O)(C)(C)C.[CH2:38]([C:40]([O-:42])=[O:41])[CH3:39]>ClC(Cl)C>[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]3[CH:33]=[CH:32][C:31]4[NH:30][C:29](=[O:34])[C:28]5[NH:35][CH:36]=[CH:37][C:27]=5[C:26]=4[CH:25]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.[CH2:38]([C:40]([O-:42])=[O:41])[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86627577HCID 86627577, compound

Product 1

HCID 86627576HCID 86627576, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1 mL of trifluoroacetic acid is added to a solution of 70 mg (0.15 mmol) 8-(1-tert-butoxycarbonyl-1H-indol-5-yl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 4 mL of dichloroethane. The solution is stirred for 2 hours at room temperature then the precipitate that forms is filtered and washed with diethyl ether to give 26 mg (45%) of 8-(1H -indol-5-yl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a brown solid.

Workup

  1. filtrationthe precipitate that forms is filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7789f6694e1b4756934dc0352da11008
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…