Diisopropylaniline → HCID 58409409, 화합물

HRID 1026364노트

반응식

HRID 1026364 반응식
CC(C)([O-])C.[Na+].[CH:7]([C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:11]=1[NH2:12])([CH3:9])[CH3:8].Br[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[CH:28][CH:27]=[CH:26]2>C1(C)C=CC=CC=1>[CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:10]([CH:7]([CH3:9])[CH3:8])[C:11]=1[NH:12][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[CH:28][CH:27]=[CH:26]2)([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 32484DiisopropylanilineHCID 1401098-BromoquinolineHCID 23676156Sodium t-butoxide

생성물 1

HCID 58409409HCID 58409409, 화합물수율 38%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Charge a round bottomed flask equipped with a reflux condenser with tris(dibenzylidene acetone)dipalladium(0)(Pd2(dba)3) (0.090 mmol, Aldrich), racemic 2,2′-bis(diphenylphosphine)-1,1′-binaphthyl (rac-BINAP) (0.207 mmol; Fluka division of Aldrich), and sodium tertiary-butoxide (NaOtBu) (4.05 mmol; Aldrich) in toluene (15 mL). To the resulting suspension add 2,6-diisopropylaniline (2.88 mmol) and 8-bromoquinoline (2.88 mmol), and then heat the resulting mixture under reflux overnight. Pump down the reaction mixture to dryness under vacuum, and purify the resulting crude residue by column chromatography on silica gel eluting with 9:1 pentane:diethyl ether (C5H12:Et2O) to give purified (1) in 38% yield.

후처리

  1. additionCharge a round bottomed flask
  2. temperatureheat the resulting mixture
  3. temperatureunder reflux overnight
  4. custompurify the resulting crude residue by column chromatography on silica gel eluting with 9:1 pentane
  5. customdiethyl ether (C5H12:Et2O) to give
  6. custompurified (1) in 38% yield

출처 및 근거

ORD 기록
ord-a96733cda8244305ab238f8e8974ba3e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729201B2

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