Sodium Carbonate → HCID 86723587, 화합물

HRID 918915노트

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HRID 918915 반응식
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10](Br)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[C:25](B(O)O)=[C:24]([CH3:29])[O:23][N:22]=1.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>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]([C:25]2[C:21]([CH3:20])=[N:22][O:23][C:24]=2[CH3:29])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 86723586HCID 86723586, 화합물

생성물 1

HCID 86723587HCID 86723587, 화합물수율 56.5%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
90 °C

실험 절차

A mixture of 7-benzyl-5-bromo-1,7-naphthyridin-8(7H)-one (0.574 g, 1.82 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (0.385 g, 2.73 mmol) and Na2CO3 (0.579 g, 5.46 mmol) was degassed under nitrogen. Then toluene (30 mL), ethanol (30 mL) and water (3 mL) were added. The reaction mixture was degassed again and Pd(PPh3)4 (0.210 g, 0.12 mmol) was added and degassing procedure was repeated. The reaction was stirred at 90° C. for 6 h under nitrogen. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was washed with water then brine, dried over Na2SO4, and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, dichloromethane to 97:3 dichloromethane/methanol) to give 7-benzyl-5-(3,5-dimethylisoxazol-4-yl)-1,7-naphthyridin-8(7H)-one (0.341 g, 56%) as a tan solid: mp 168-170° C.; 1H NMR (400 MHz, CDCl3): δ 8.92-9.00 (m, 1H), 7.52-7.60 (m, 2H), 7.29-7.42 (m, 5H), 7.04 (s, 1H), 5.26-5.43 (m, 2H), 2.22 (s, 3H), 2.04 (s, 3H); ESI MS m/z 332.0 [M+H]+.

후처리

  1. customwas degassed under nitrogen
  2. additionThen toluene (30 mL), ethanol (30 mL) and water (3 mL) were added
  3. customThe reaction mixture was degassed again
  4. customdegassing procedure
  5. temperatureAfter that time the reaction was cooled to rt
  6. concentrationconcentrated under reduced pressure
  7. additiondiluted with water (50 mL)
  8. extractionextracted with ethyl acetate (2×100 mL)
  9. washThe organic phase was washed with water
  10. dry with materialbrine, dried over Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customThe product was purified by flash column chromatography (silica gel, dichloromethane to 97:3 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-cffbd76a41a34490b602a7815745c9d0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271978B2

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