Trifluoroacetic acid → HCID 68760289, compound

HRID 79511Notes

Reaction equation

HRID 79511 reaction equation
[Br:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[Br:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68760498tert-butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68760289HCID 68760289, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.40 g, 1.05 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added. The reaction was stirred at room temperature for 1 hour and 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 was collected by filtration, washed with ether, and dried to give 5-bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.28 g, 94.9% yield) 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
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-cb7081c9bff74ddc917b841ac0a59369
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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