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

HRID 79597Notes

Reaction equation

HRID 79597 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68762312HCID 68762312, compound

Product 1

HCID 687620895-(2-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridineYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.045 g, 0.11 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added, and the reaction was stirred at room temperature for 1 hour and concentrated to dryness. The resulting residue was then dissolved in minimal DCM and added to a stirring solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to give 5-(2-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.034 g, 81% yield).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was then dissolved in minimal DCM
  3. additionadded to a stirring solution of 1M HCl in ether
  4. filtrationThe resulting solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-ba69b55850e843d795c6b50f7e19d0bb
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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