Cesium carbonate → 5-(3-Chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine

HRID 1710692ノート

反応式

HRID 1710692 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.[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[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

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 38618773-Chloro-4-pyridineboronic acidHCID 594576145-Bromo-6-(3-fluorophenyl)pyrazin-2-amine

生成物 1

HCID 160715405-(3-Chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine収率 39%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A microwave oven reactor was charged with 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1, 0.3 g, 1.11 mmol), (3-chloropyridin-4-yl)boronic acid (212 mg, 1.03 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride dichloromethane complex (1:1) (39 mg, 0.047 mmol), dioxane (8 mL) and a 1.2M aqueous solution of cesium carbonate was added (1.9 mL, 2.39 mmol). The mixture was heated to 150° C. for 10 min in the microwave oven, then 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 to dichloromethane/methanol 90:10) furnished the title compound as a yellowish solid (78 mg, 39%).

後処理

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. extractionthe aqueous phase extracted twice with ethyl acetate
  4. washthe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-f00dfefcb4164b419097fc71b7024368
出典データセット
uspto-grants-2010_09
特許番号
US07790728B2

反応ノート

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