2-(Tributylstannyl)furan → 4-Furan-2-yl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642345노트

반응식

HRID 642345 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:28]1[O:29][CH:30]=[CH:31][CH:32]=1)CCC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 43936882-(Tributylstannyl)furanHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 684287754-Furan-2-yl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester수율 57.9%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (248 mg, 0.66 mmole), 2-(tributylstannyl)furan (414 μl, 1.31 mmole) and bis(triphenylphosphine)-palladium(II) dichloride (46 mg, 0.06 mmole) in dimethylformamide (2.5 ml) was stirred at 130° C. for 25 min before it was cooled to room temperature, quenched with water, filtered. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (140 mg). MS: (+) m/z 367.00 (M+1).

후처리

  1. temperaturewas cooled to room temperature
  2. customquenched with water
  3. filtrationfiltered
  4. customThe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-ddc1f0c498a14ec1906b78d80d2f6500
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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