3-Bromoanisole → N-cyclopropyl-3-methoxyaniline

HRID 1036609ノート

反応式

HRID 1036609 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 45091015N-cyclopropyl-3-methoxyaniline

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c90029e9c65044fe9888563b98cccf2f
出典データセット
uspto-grants-2013_10
特許番号
US08546414B2

反応ノート

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