Ethanol → [2-(4-Ethoxycarbonyl-4-methylpiperidin-1-yl)pyrimidin-5-yl]boronic acid

HRID 626933

반응식

HRID 626933 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.Cl.[CH3:12][C:13]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O)C.C(N(CC)CC)C>CO.ClCCl.ClCCl>[CH2:22]([O:21][C:19]([C:13]1([CH3:12])[CH2:18][CH2:17][N:16]([C:2]2[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1)=[O:20])[CH3:23]

참가 물질

7

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 19361804Ethyl 4-methylpiperidine-4-carboxylate hydrochlorideHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

생성물 1

HCID 89923723[2-(4-Ethoxycarbonyl-4-methylpiperidin-1-yl)pyrimidin-5-yl]boronic acid수율 61%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
80 °C

실험 절차

To 2-chloropyrimidine-5-boronic acid (4.00 g, 25.3 mmol) were added ethyl 4-methylpiperidine-4-carboxylate hydrochloride (4.09 g, 23.9 mmol), ethanol (40 mL) and triethylamine (9.0 mL, 64.0 mmol). The mixture was heated at 80° C. for 3 h before being concentrated in vacuo. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL), then the aqueous layer was separated and extracted with ethyl acetate (2×100 mL). The organic layers were combined and washed with brine (100 mL), then dried (Na2SO4). The solvent was then removed under reduced pressure and the crude reaction mixture was purified by flash column chromatography on silica (Biotage SNAP 100 g, Isolera). Gradient elution, with 100% dichloromethane to 30% methanol/dichloromethane, afforded the title compound (4.27 g, 43% yield, 74% purity) as a brown oil. LCMS (pH 10): MH+ m/z 294.1, RT 0.652 minutes.

후처리

  1. concentrationbefore being concentrated in vacuo
  2. customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. customthe aqueous layer was separated
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was then removed under reduced pressure
  8. customthe crude reaction mixture
  9. customwas purified by flash column chromatography on silica (Biotage SNAP 100 g, Isolera)
  10. washGradient elution

출처 및 근거

ORD 기록
ord-c481efd5e3b44959ac351b257e6d3236
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309243B2

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