Cesium carbonate → 6-(3-Fluorophenyl)-5-pyridin-4-ylpyrazin-2-amine

HRID 1710691ノート

反応式

HRID 1710691 の反応式
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[F:14][C:10]1[CH:9]=[C:8]([C:7]2[N:6]=[C:5]([NH2:15])[CH:4]=[N:3][C:2]=2[C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 594576145-Bromo-6-(3-fluorophenyl)pyrazin-2-amine

生成物 1

HCID 160715396-(3-Fluorophenyl)-5-pyridin-4-ylpyrazin-2-amine収率 60.2%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

An oven dried resealable Schlenk tube was charged with 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1, 0.3 g, 1.11 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (459 mg, 2.23 mmol), dioxane (35 mL) and a 2M aqueous solution of cesium carbonate (3.3 mL, 6.66 mmol) were added. The Schienk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex [PdCl2dppf.DCM] (45 mg, 0.055 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 20 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane/methanol 98:2 to dichloromethane/methanol 95:5) provided the title compound as a yellowish solid (178 mg, 60%)

後処理

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 100° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase extracted twice with ethyl acetate the organic layers
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

出典と根拠

ORDレコード
ord-dc1fa82158f1447095690ad184f83115
出典データセット
uspto-grants-2010_09
特許番号
US07790728B2

反応ノート

読み込み中…