Trifluoroacetic acid → methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 79515Notes

Reaction equation

HRID 79515 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[C:16]3[N:24](C(OC(C)(C)C)=O)[CH:25]=[CH:26][C:15]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:11]1([C:14]2[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[C:16]3[NH:24][CH:25]=[CH:26][C:15]=23)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68760599HCID 68760599, compound

Product 1

HCID 68762011methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butyl 5-methyl 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-1,5-dicarboxylate (0.34 g, 0.74 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.5 mL) was then added. The reaction was stirred at room temperature for 4 hours and then concentrated to dryness. The resulting residue was dissolved in minimal DCM and added to a stirring solution of 1M HCl in ether. The resulting solid methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.19 g, 98.9% yield) was collected and dried as the dihydrochloride salt.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was dissolved in minimal DCM
  3. additionadded to a stirring solution of 1M HCl in ether

Sources & evidence

ORD record
ord-a9069229037e4e49834883126da06c47
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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