Cesium carbonate → 5-Bromo-3-(5-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 407674

반응식

HRID 407674 반응식
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([NH2:8])[CH:4]=1)[CH3:2].Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([Br:16])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:16][C:14]1[CH:15]=[C:10]([NH:8][C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[NH:7][N:6]=2)[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 219910953-ethyl-1H-pyrazol-5-amine

생성물 1

HCID 670161795-Bromo-3-(5-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one수율 43%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (80 mL), 5-ethyl-1H-pyrazol-3-amine (3.33 g, 30.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (9.6 g, 36 mmol), and cesium carbonate (19.5 g, 60 mmol). After bubbling nitrogen through the suspension for 10 minutes, Xantphos (1.73 mg, 3.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.36 mg, 1.5 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 2 h. It was then filtered immediately. The solid was washed with dioxane (3×30 mL) and the combined filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (2:1 to 1:2) to afford 122a (3.8 g, 43%) as a red solid. MS-ESI: [M+H]+ 297.0

후처리

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter bubbling nitrogen through the suspension for 10 minutes
  3. customflush
  4. temperatureheated
  5. temperatureat reflux for 2 h
  6. filtrationIt was then filtered immediately
  7. washThe solid was washed with dioxane (3×30 mL)
  8. concentrationthe combined filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica-gel column chromatography
  10. washeluting with petroleum ether/ethyl acetate (2:1 to 1:2)

출처 및 근거

ORD 기록
ord-e96e3f51904445afb841d15716e27d1d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754077B2

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