Water → cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyrazinyl]morpholine

HRID 2278419노트

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HRID 2278419 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:13]=[CH:12][O:11][C:10]=2[CH3:14])O1.Cl[C:17]1[N:22]=[C:21]([N:23]2[CH2:28][C@H:27]([CH3:29])[O:26][C@H:25]([CH3:30])[CH2:24]2)[CH:20]=[N:19][CH:18]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH3:30][C@H:25]1[O:26][C@@H:27]([CH3:29])[CH2:28][N:23]([C:21]2[CH:20]=[N:19][CH:18]=[C:17]([C:9]3[CH:13]=[CH:12][O:11][C:10]=3[CH3:14])[N:22]=2)[CH2:24]1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 242295474,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolaneHCID 86702421cis-4-(6-Chloro-2-pyrazinyl)-2,6-dimethylmorpholine

생성물 1

HCID 67513262cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyrazinyl]morpholine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

4,4,5,5-Tetramethyl-2-(2-methyl-3-furanyl)-1,3,2-dioxaborolane (567 mg, 2.72 mmol) was added to a solution of cis-4-(6-chloro-2-pyrazinyl)-2,6-dimethylmorpholine (620 mg, 2.72 mmol) in a mixture of 1,4-dioxane (17 mL), water (2.83 mL) and sodium carbonate (577 mg, 5.45 mmol). The solution was degassed using argon gas and then charged with tetrakis(triphenylphosphine)palladium(0) (315 mg, 0.272 mmol). After addition, the reaction mixture was stirred and heated in the microwave at 100° C. for 1 hour. Crude LCMS shows desired product and starting material so the reaction mixture was stirred and heated for a further 1 hour at 100° C. in the microwave. Crude LCMS shows desired product and no starting material can be seen. The reaction mixture washed with ethyl acetate (200 mL), water (100 mL), filtered and then evaporated to dryness. The residue was dissolved in dichloromethane (˜5 ml) and purified on silica by a Biotage SP4 chromatographic system (40+M cartridge, eluted with 0-50% ethyl acetate in isohexanes). Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound (441 mg, 1.533 mmol, 56.3% yield). LC/MS [M+H]+=274.

후처리

  1. customThe solution was degassed
  2. additionAfter addition

출처 및 근거

ORD 기록
ord-034b285680af4b9ba3965068025f0d70
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133178B2

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