Toluene → tert-Butyl[3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

HRID 41271

반응식

HRID 41271 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([CH3:19])=[N:10][N:11]2[C:15](Br)=[C:14]([S:17][CH3:18])[S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([CH2:36][O:37][CH3:38])[CH:33]=[C:32]([O:39][CH3:40])[C:31]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)(=O)C.O.C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([CH3:19])=[N:10][N:11]2[C:15]([C:31]3[C:32]([O:39][CH3:40])=[CH:33][C:34]([CH2:36][O:37][CH3:38])=[CH:35][C:30]=3[O:29][CH3:28])=[C:14]([S:17][CH3:18])[S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 230809452,6-Dimethoxy-4-methoxymethylphenylboric acidHCID 58223503HCID 58223503, 화합물

생성물 1

HCID 68166681tert-Butyl[3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate수율 91.3%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

To a mixture of tert-butyl[3-bromo-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate (397 mg, 1.03 mmol), toluene (6.8 mL) and ethanol (3.4 mL) were added 2,6-dimethoxy-4-(methoxymethyl)phenylboric acid (349 mg, 1.55 mmol) synthesized by the method described in WO2004/037822, a 1M aqueous solution of sodium carbonate (2.06 mL, 2.06 mmol) and tetrakis(triphenylphosphine)palladium (119 mg, 0.10 mmol) in this order, and the mixture was heated to reflux at 110° C. for three hours. Water was added to the reaction mixture and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was stirred at 75° C. for five hours. Chloroform was added to the reaction mixture, insoluble matters were filtered off, and then the solvent was distilled off under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate: 33% then 66%) to obtain 450.9 mg (0.94 mmol) of the title compound.

후처리

  1. customsynthesized by the method
  2. customthe organic layer was separated
  3. stirringthe organic layer was stirred at 75° C. for five hours
  4. additionChloroform was added to the reaction mixture, insoluble matters
  5. filtrationwere filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-066a6d4ffd9c437e8db80eb335421739
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530504B2

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