Toluene → 3-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-[1-(2,5-dimethoxy-phenyl)-cyclopropyl]-2-methyl-pyrazine

HRID 1593529Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[C:11]1[N:16]=[C:15](N2C3C=CC=CC=3N=N2)[CH:14]=[N:13][C:12]=1[CH3:26].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=1[Mg]Br.[C:39]1([CH3:45])C=CC=C[CH:40]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[C:11]1[C:12]([CH3:26])=[N:13][CH:14]=[C:15]([C:45]2([C:30]3[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=3[O:28][CH3:27])[CH2:39][CH2:40]2)[N:16]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 46 mg 1-[6-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-methyl-pyrazin-2-yl]-1H-benzotriazole (0.12 mmol) in 200 μL toluene was added 100 μL 0.5 M 2,5-dimethoxyphenyl magnesium bromide in THF. The solution is subjected three times to 3 GHz microwave radiation heating to 150° C. for 15 min. After quenching with saturated ammonium chloride, the organic phase was directly subjected to column chromatography eluting with hexanes DCM followed by hexane ethyl acetate (0.1% Et3N) . Fractions containing the desired product were pooled and concentrated to give a residue that was further purified by RP—HPLC eluting with acetonitrile water (0.03% TFA) giving 2.6 mg of the title compound.

Workup

customAfter quenching with saturated ammonium chloride
washeluting with hexanes DCM
additionFractions containing the desired product
concentrationconcentrated
customto give a residue that
customwas further purified by RP—HPLC
washeluting with acetonitrile water (0.03% TFA)

Sources & evidence

ORD record: ord-79476fa1ac2043978924ebd12a2b219a
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297708B2

Reaction notes

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