Acetic Acid → 4-((1-benzylpiperidin-3-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1854491Notes

Reaction equation

HRID 1854491 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]3[N:23]([Si](C(C)C)(C(C)C)C(C)C)[CH:24]=[CH:25][C:17]=23)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][NH2:37].CC(O)=O>CCO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[N:36][NH2:37])[C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]3[NH:23][CH:24]=[CH:25][C:17]=23)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 58010051(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone

Product 1

HCID 866371884-((1-benzylpiperidin-3-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridineYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.45 g, 2.84 mmol), anhydrous hydrazine (0.273 g, 8.53 mmol) and AcOH (0.163 mL, 2.84 mmol) was heated in EtOH (35 mL) at reflux for about 16 h. The reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (60 mL). The organic phase was washed with brine (40 mL) and concentrated to yield 4-((1-benzylpiperidin-3-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (1.04 g, quantitative) as a brown amorphous solid that was used directly in the next step without further purification: LC/MS (Table 2, Method a) Rt=1.57 min; MS m/z: 368 (M+H)+.

Workup

  1. temperatureat reflux for about 16 h
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (60 mL)
  4. washThe organic phase was washed with brine (40 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0670c17054e74b45b6da7515c0c05c26
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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