Tetrahydrofuran → 1-(6-Chloropyridazin-3-yl)ethan-1-one

HRID 2038760Notes

Reaction equation

HRID 2038760 reaction equation
[Cl:1][C:2]1[N:7]=[N:6]C(C#N)=CC=1.[CH3:10][Mg]Br.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[Cl:1][C:2]1[N:7]=[N:6][C:13]([C:17](=[O:16])[CH3:10])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 133828716-Chloropyridazine-3-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 468356481-(6-Chloropyridazin-3-yl)ethan-1-one

Procedure

A solution of 6-chloro-pyridazine-3-carbonitrile (prepared according to MacDonald et al., WO/2008/068277) (100 mg, 0.71 mmol) in dry THF (3.6 mL) was cooled to −50° C. in a dry ice/acetone bath. Methylmagnesium bromide (1.0 M in MePh/THF, 0.54 mL, 0.75 mmol) was added via syringe in one portion. The cold bath was removed and the reaction was stirred for 1.5 h. To the reaction mixture was added saturated aqueous NH4Cl and this mixture was extracted with EtOAc (3×). The combined organics were dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2) to give 34 mg of 1-(6-chloro-pyridazin-3-yl)-ethanone as a brown semi-solid, m/z 157.3 [M+H]+.

Workup

  1. customThe cold bath was removed
  2. additionTo the reaction mixture was added saturated aqueous NH4Cl
  3. extractionthis mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c522e294b1c944cfb89f43ad5a88cddb
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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