Potassium Carbonate → Ethyl 6-isobutyl-3-methylpyrazine-2-carboxylate

HRID 869724

反応式

HRID 869724 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([CH3:13])=[N:4][CH:3]=1.[CH2:14](B(O)O)[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.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]>[CH2:14]([C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([CH3:13])=[N:4][CH:3]=1)[CH:15]([CH3:17])[CH3:16]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734395(2-Methylpropyl)boronic acidHCID 87384166Ethyl 6-chloro-3-methylpyrazine-2-carboxylate

生成物 1

HCID 67395659Ethyl 6-isobutyl-3-methylpyrazine-2-carboxylate

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A suspension of ethyl 6-chloro-3-methylpyrazine-2-carboxylate (1.94 g, 9.67 mmol), isobutylboronic acid (1.97 g, 19.3 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(212 mg, 0.290 mmol), and potassium carbonate (2.67 g, 19.3 mmol) in 1,4-dioxane (30 mL) was heated at 100° C. for 4.5 h. After being cooled to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtrated through celite with ethyl acetate. The filtrate was combined and concentrated in vacuo. The residue was diluted ethyl acetate, and washed with saturated aqueous sodium bicarbonate and saturated brine, dried over sodium bicarbonate, filtrated and concentrated in vacuo. The residue was dissolved to dichloromethane, and the insoluble materials were filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:1) to give ethyl 6-isobutyl-3-methylpyrazine-2-carboxylate. MS (APCI): m/z 223 (M+H).

後処理

  1. temperatureAfter being cooled to ambient temperature
  2. filtrationfiltrated through celite with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. washwashed with saturated aqueous sodium bicarbonate and saturated brine
  5. dry with materialdried over sodium bicarbonate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved to dichloromethane
  9. filtrationthe insoluble materials were filtered off
  10. concentrationThe filtrate was concentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:1)

出典と根拠

ORDレコード
ord-cb42aecc7f1b48e6836d3092f75b0c14
出典データセット
uspto-grants-2015_03
特許番号
US08969376B2

関連ノート

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