Pyridine → HCID 86689824, compound

HRID 2409015Notes

Reaction equation

HRID 2409015 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=O)[CH:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl.[NH2:23][OH:24].N1C=CC=CC=1>CCO>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=[N:23][OH:24])[CH:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86689825HCID 86689825, compound

Product 1

HCID 86689824HCID 86689824, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.58 g, 1.93 mmol) in EtOH (5 mL) was added hydroxylamine hydrochloride (0.7 g, 9.6 mmol) and pyridine (0.5 mL). The reaction mixture was heated at 70° C. for 18 h and then the solvent was removed under reduced pressure to afford 0.6 g (98%) of 1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde oxime as white solid which was used in the next step without further purification. MS (ESI) m/z: 316.2 [M+1]+.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-666e06350582432ab18d4e64bec2b30b
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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