Methyl 5-bromo-2-chloronicotinate → HCID 68008409、化合物

HRID 533145ノート

反応式

HRID 533145 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 68008409HCID 68008409、化合物

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-fddfa0fbe793432fa1738d92589172dc
出典データセット
uspto-grants-2014_10
特許番号
US08853237B2

反応ノート

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