Sodium Carbonate → 2-[4-(Trifluoromethyl)phenyl]pyrazine

HRID 1869768노트

반응식

HRID 1869768 반응식
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:20])([F:19])[C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Cl-].[Cl-].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Pd+2]>[F:8][C:9]([F:20])([F:19])[C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 73277ChloropyrazineHCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 50458142-[4-(Trifluoromethyl)phenyl]pyrazine

시약·촉매·용매 2

HCID 178478644HCID 178478644, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of chloropyrazine (10, 0.087 mol), 4-(trifluoromethyl)phenylboronic acid (21 g), palladium(diphenylphosphino)ferrocene dichloride (3.5 g, 5 mol %) and sodium carbonate (100 mL, 2M) in dioxane (200 mL) was degassed (×3) via Firestone valve. The mixture was heated under reflux for 1 h., evaporated in vacuo, the residue partitioned between ethyl acetate and water, then the organic phase was washed with brine, dried (MgSO4) and evaporated. The black residue was dry-loaded onto silica and purified by elution with 5-25% ethyl acetate in iso-hexane. This afforded the product as white crystals.

후처리

  1. customwas degassed (×3) via Firestone valve
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 h.
  4. customevaporated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. washthe organic phase was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. custompurified by elution with 5-25% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-a764eaa7aee84b359078935a8acc89f5
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638629B2

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