Dichloromethane → 5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride

HRID 79565Notes

Reaction equation

HRID 79565 reaction equation
[C:1]1([C:7]2[C:8]([N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:37]>>[ClH:37].[ClH:37].[C:1]1([C:7]2[C:8]([N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68764043HCID 68764043, compound

Product 1

HCID 687587805-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochlorideYield 94.3%

Procedure

tert-Butyl 4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.40 g, 1.06 mmol) was placed in DCM (10 mL). TFA (2 mL) was then added, and the reaction was stirred for 1 hour. The reaction was concentrated to dryness, redissolved 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-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride (0.350 g, 94.3% yield).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved 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-4c815f92a32442edbbe2959cf19c1ac2
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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