Formaldehyde → 2-[4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-piperazinyl]benzonitrile

HRID 1828281Notes

Reaction equation

HRID 1828281 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[N:10]1([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:24]([O-])(=O)C.[Na+].C=O.[OH-].[Na+]>O.C(O)(=O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:24][N:13]2[CH2:14][CH2:15][N:10]([C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])[CH2:11][CH2:12]2)=[CH:2]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 220659752-[4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-piperazinyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1H-pyrrolo[2,3-b]pyridine (47 mg, 0.40 mmol), 2-(1-piperazinyl)benzonitrile (65 mg, 0.48 mmol), sodium acetate (72 mg, 0.53 mmol), and formaldehyde (0.48 mmol) were combined in water and glacial acetic acid (1:2, 1 mL) and stirred at room temperature for 18 hours. The mixture was treated with a solution of 2M NaOH and concentrated under reduced pressure. The residue was treated with hot methanol. The methanol was filtered and the filter cake was washed with cold methanol to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.62 (m, 4H) 3.14 (m, 4H) 4.03 (s, 2H) 5.60 (s, 1H) 7.09 (m, 3H) 7.61 (m, 2H) 8.06 (dd, J=8.31, 1.53 Hz, 1H) 8.20 (dd, J=4.75, 1.70 Hz, 1H). (ESI) m/z 318 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with hot methanol
  3. filtrationThe methanol was filtered
  4. washthe filter cake was washed with cold methanol

Sources & evidence

ORD record
ord-4c9b147ce2554be5a7ada2279ad49f83
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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