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

HRID 79556Notes

Reaction equation

HRID 79556 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[NH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:9]=2[N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68761367tert-butyl 4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 687614063-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridineYield 120.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.390 g, 0.994 mmol) was placed in DCM (10 mL) at room temperature. TFA (1 mL) was added, and the reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness, dissolved in minimal DCM, and added dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give 3-methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.350 g, 96.4% yield), which was used without further purification.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutiondissolved in minimal DCM
  3. additionadded dropwise to a stirring solution of 1M HCl in ether
  4. filtrationThe solid product was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-eb18949c43d64b7498fe4c0d49738ec6
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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