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

HRID 1593529노트

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HRID 1593529 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-79476fa1ac2043978924ebd12a2b219a
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297708B2

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