Water → 1-(Pyridazin-3-yl)ethan-1-ol

HRID 1503428Notes

Reaction equation

HRID 1503428 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[C:13]([Cu])#N.O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([OH:5])[CH3:13])[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 58197546N-methoxy-N-methylpyridazine-3-carboxamideHCID 178418546HCID 178418546, compound

Product 1

HCID 151975111-(Pyridazin-3-yl)ethan-1-olYield 168.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of compound 2 (100 mg, 0.22 mmol) in DMF (10 mL) was added CuCN (40 mg, 0.44 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol) under N2 at room temperature. The resulting mixture was stirred 30 min at 180° C. in a microwave reactor. Water (15 mL) was added and the mixture was extracted with EtOAc (3×20 mL), and the combined organic layers were dried over Na2SO4 and concentrated to give the residue which was purified by preparative TLC on silica gel (petroleum ether:ethyl acetate=5:1) to give compound 3 (46 mg, 52%) as a white solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give the residue which
  5. customwas purified by preparative TLC on silica gel (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-87d3eb0dca4a41c4a86fb421a351189d
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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