3-Bromoanisole → N-cyclopropyl-3-methoxyaniline

HRID 1036609노트

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HRID 1036609 반응식
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:10]1([NH:13][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)[CH2:12][CH2:11]1

참가 물질

7

반응물 4

HCID 169713-BromoanisoleHCID 69828CyclopropylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

생성물 1

HCID 45091015N-cyclopropyl-3-methoxyaniline

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a high-pressure tube was added 3-bromoanisole (0.250 mL, 2 mmol), cyclopropylamine (0.225 mL, 3.2 mmol), sodium t-butoxide (0.29 g, 3.0 mmol), (+/−) BINAP (0.04 g, 0.06 mmol), and Pd2(dba)3 (0.010 g, 0.01 mmol). This mixture was suspended in 4 mL anhydrous toluene. The tube was flushed with dry nitrogen gas, then capped and wrapped in aluminum foil. The reaction mixture was stirred and heated to 80° C. overnight, then allowed to cool, and the reaction vessel was opened. The mixture was diluted with diethyl ether, filtered through Celite, and the filtrate was concentrated to a yellow oil. LC/MS analysis showed one peak with the correct mass, and due to the limited stability of the material, it was carried through without further purification. FIA MS 164 (M+1).

후처리

  1. customThe tube was flushed with dry nitrogen gas
  2. customcapped
  3. temperatureto cool
  4. additionThe mixture was diluted with diethyl ether
  5. filtrationfiltered through Celite
  6. concentrationthe filtrate was concentrated to a yellow oil
  7. customdue to the limited stability of the material, it was carried through without further purification

출처 및 근거

ORD 기록
ord-c90029e9c65044fe9888563b98cccf2f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546414B2

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