Methyl 5-bromo-2-chloronicotinate → HCID 68008409, 화합물

HRID 533145노트

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HRID 533145 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:13]([B-](F)(F)F)=[CH2:14].[K+]>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Br:1])[CH:3]=[N:4][C:5]=1[CH:13]=[CH2:14]

참가 물질

5

반응물 2

HCID 2763343Methyl 5-bromo-2-chloronicotinateHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 68008409HCID 68008409, 화합물

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

Methyl 5-bromo-2-chloronicotinate (500 mg, 2.0 mmol) was dissolved in EtOH (20 mL) with potassium vinyltrifluoroborate (269 mg, 2.0 mmol), TEA (0.28 mL, 2.0 mmol), and [1,1′-Bis (diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (29 mg, 0.04 mmol). The reaction was heated at 80° C. for 1 h, filtered through a Celite pad. The filtrate was concentrated, partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated, dried over MgSO4 and concentrated. Purification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%) affords the compound, methyl-5-bromo-2-vinylnicotinate, as a white solid (484 mg, 76%). LC-MS (M+H)=242.1.

후처리

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between EtOAc (50 mL) and H2O (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%)

출처 및 근거

ORD 기록
ord-fddfa0fbe793432fa1738d92589172dc
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853237B2

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