HCID 67540191, compound → HCID 20784473, compound

HRID 1192334Notes

Reaction equation

HRID 1192334 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH:21]=[CH:22][C:15]=23)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[N:11]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH:21]=[CH:22][C:15]=23)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 67540191HCID 67540191, compound

Product 1

HCID 20784473HCID 20784473, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 4-(4-benzyl-piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (3.90 g, 13.3 mmol) and Pd(OH)2/C (937 mg, 1.33 mmol) in MeOH (60 mL) was stirred under 1 atmosphere of H2 for 2 d. The mixture was diluted with MeOH, filtered through diatomaceous earth, and the filtrate was concentrated in vacuo to give 4-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine as a solid (100 mg kept as free base). The remaining material was suspended in MeOH and treated with 2.0 M HCl in Et2O. This mixture was concentrated in vacuo to give 4-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine dihydrochloride (2.30 g). 1H NMR (DMSO-d6, 400 MHz) δ 11.5 (bs, 1H), 9.43 (bs, 2H), 7.96 (d, J=5.4 Hz, 1H), 7.25 (d, J=3.3 Hz, 1H), 6.49 (d, J=3.4 Hz, 1H), 6.45 (d, J=5.4 Hz, 1H), 3.56 (bs, 4H), 3.21 (bs, 4H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-900a31b146e64f878c657b24a8558309
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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