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

HRID 85072Notes

Reaction equation

HRID 85072 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)[N:12]([S:39]([C:42]4[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=4)(=[O:41])=[O:40])[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:20]=[CH:21][C:22]([CH2:23][N:24]6[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]6)=[CH:37][CH:38]=5)[CH:17]=4)[N:12]([S:39]([C:42]4[CH:43]=[CH:44][C:45]([CH3:46])=[CH:47][CH:48]=4)(=[O:41])=[O:40])[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70115940tert-butyl 4-(4-(3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperazine-1-carboxylate

Product 1

HCID 701157013-(1H-indol-5-yl)-5-(4-(piperazin-1-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-(4-(3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperazine-1-carboxylate (500 mg) was suspended in 6 mL of dichloromethane and treated with TFA (5 mL) and reacted for 30 minutes. The solvent was removed in vacuo and the residue washed with 1 N sodium hydroxide solution, water and brine and dried over MgSO4 to yield 418 mg of crude product that was used without further purification (562 M+H).

Workup

  1. customreacted for 30 minutes
  2. customThe solvent was removed in vacuo
  3. washthe residue washed with 1 N sodium hydroxide solution, water and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6118d83a52ee420dbefb084eaf4a8fdb
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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