Potassium Acetate → 1-(Pyridazin-3-yl)ethan-1-ol

HRID 1503426Notes

Reaction equation

HRID 1503426 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[CH3:13]C([O-])=O.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([OH:5])[CH3:13])[N:7]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 58197546N-methoxy-N-methylpyridazine-3-carboxamide

Product 1

HCID 151975111-(Pyridazin-3-yl)ethan-1-olYield 281.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of compound 2 (170 mg, 0.4 mmol), compound 2A (112 mg, 0.44 mmol), PdCl2(dppf)2 (50 mg, 0.08 mmol) and KOAc (118 mg, 1.2 mmol) in anhydrous 1,4-dioxane (6 mL) was heated at 100° C. for 60 min in a CEM microwave reactor. The mixture was concentrated in vacuo and the residue was purified by preparative TLC (eluent:petroleum ether:ethyl acetate=3:1) to give compound 3 (140 mg, 70%, 67% purity) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by preparative TLC (eluent:petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-af32eae46ade4dfa883d25c80222f3fd
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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