HCID 59596423, compound → HCID 59596607, compound

HRID 2264945Notes

Reaction equation

HRID 2264945 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[C:11](Cl)[N:10]=[N:9][C:8]=2[C:7]=1[OH:17])=[O:5])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[N:9][C:8]=2[C:7]=1[OH:17])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59596423HCID 59596423, compound

Product 1

HCID 59596607HCID 59596607, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 10% wt. palladium on carbon (150 mg) in ethanol was added to a de-gassed suspension of 3-chloro-7-hydroxy-5-methyl-5H-pyrrolo[3,2-c]pyridazine-6-carboxylic acid ethyl ester (1.6 g, 6.26 mmol) in ethanol (150 mL), the atmosphere evacuated and back-filled with nitrogen, re-evacuated and back-filled with hydrogen and the mixture stirred under hydrogen (1 atmosphere) for 3 days at room temperature. The resultant mixture was filtered through Celite® with DCM/methanol washings, the filtrate concentrated in vacuo to give the title compound as a yellow solid (1.4 g, quantitative). LCMS (method B): RT=1.53/1.65 min, M+H+=222.

Workup

  1. customthe atmosphere evacuated
  2. additionback-filled with nitrogen
  3. customre-evacuated
  4. additionback-filled with hydrogen
  5. filtrationThe resultant mixture was filtered through Celite® with DCM/methanol washings
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-68a1f8c79aef4c28ae8cfef23b9d2c6a
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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