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

HRID 1942307ノート

反応式

HRID 1942307 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178478644HCID 178478644、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

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 (100mL, 2M) in dioxane (200 mL) was degassed (×3) via Firestone valve. The mixture was heated under reflux for 1 h. Dioxane was removed in vacuo. The residue was dispersed between ethyl acetate and water and 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. 1H NMR (400 MHz, CDCl3): δ 7.78 (2H, d, J 8.2), 8.15 (2H, d, J 8.2), 8.59 (1H, d, J 2.5), 8.68 (1H, t, J 2.0), 9.08 (1H, d, J 1.4).

後処理

  1. customwas degassed (×3) via Firestone valve
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 h
  4. customDioxane was removed in vacuo
  5. additionThe residue was dispersed 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

出典と根拠

ORDレコード
ord-78040d2a91b2469fad6c6e7e846e8914
出典データセット
uspto-grants-2013_03
特許番号
US08389547B2

反応ノート

読み込み中…