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4-Chloroaniline → HCID 25230563, 화합물

HRID 1961716
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HRID 1961716 반응식
Cl[C:2]1[C:3]([CH2:15][O:16][CH3:17])=[N:4][CH:5]=[C:6]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)[N:7]=1.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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]>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[C:3]([CH2:15][O:16][CH3:17])=[N:4][CH:5]=[C:6]([N:8]3[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]3)[N:7]=2)=[CH:21][CH:20]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 78124-ChloroanilineHCID 10796Cesium carbonateHCID 59570670HCID 59570670, 화합물

생성물 1

HCID 25230563HCID 25230563, 화합물수율 80%

시약·촉매·용매 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

A mixture of 3-chloro-5-(3,5-dimethyl-pyrazol-1-yl)-2-methoxymethyl-pyrazine (34 mg, 0.12 mmol), 4-chloroaniline (22 mg, 0.17 mmol) and cesium carbonate (80 mg, 0.24 mmol) in dry dioxane (2 mL) was degassed with argon for 15 minutes. Tris(dibenzylideneacetone)dipalladium (0) (3 mg, 0.003 mmol) and 1,1′-bis(diphenyl-phosphino) ferrocene (6 mg, 0.01 mmol) were added followed by degassing for 5 minutes and the reaction mixture was stirred at 120° C. over night. Dichloromethane was added and the solution was filtrated. The filtrate was concentrated in vacuo. Flash chromatography (ethyl acetate/heptane as eluent) gave (4-chloro-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-3-methoxymethyl-pyrazin-2-yl]-amine (33 mg, 80%) as a white solid.

후처리

  1. customwas degassed with argon for 15 minutes
  2. customby degassing for 5 minutes
  3. additionDichloromethane was added
  4. filtrationthe solution was filtrated
  5. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-bf649b410e994cdc9beb3e70cb29dbce
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415358B2

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