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

HRID 1710692

반응식

HRID 1710692 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f00dfefcb4164b419097fc71b7024368
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790728B2

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