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

HRID 1593529ノート

反応式

HRID 1593529 の反応式
[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

参加物

5

反応物 3

HCID 1140TolueneHCID 695133011-[6-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-methyl-pyrazin-2-yl]-1H-benzotriazoleHCID 178492591HCID 178492591、化合物

生成物 1

HCID 101594223-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-[1-(2,5-dimethoxy-phenyl)-cyclopropyl]-2-methyl-pyrazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-79476fa1ac2043978924ebd12a2b219a
出典データセット
uspto-grants-2007_11
特許番号
US07297708B2

反応ノート

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