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

HRID 85073Notes

Reaction equation

HRID 85073 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:38]=[CH:37][C:22]([CH2:23][N:24]6[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]6)=[CH:21][CH:20]=5)[CH:17]=4)[NH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(O)(C(F)(F)F)=O>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:38]=[CH:37][C:22]([CH2:23][N:24]6[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]6)=[CH:21][CH:20]=5)[CH:17]=4)[NH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46236050HCID 46236050, compound

Product 1

HCID 866916593-(1H-indol-5-yl)-5-(4-(piperazin-1-ylmethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-(4-(3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperazine-1-carboxylate (63 mg) was suspended in dichloromethane (2 mL) and treated with TFA (2 mL). The resulting mixture was stirred for 90 minutes at room temperature, after which the solvent was removed in vacuo. The residue was dissolved in EtOAc and washed with 10% sodium hydroxide solution, water, and brine. The organic layer was dried over MgSO4, and the solvent was removed in vacuo. MPLC silica gel chromatography (0-20% MeOH in dichloromethane) provided an analytical sample (10 mg, 408 M+H) of the title compound.

Workup

  1. customafter which the solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 10% sodium hydroxide solution, water, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a1fb115957cd47b58394b55621ff5043
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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