Diisopropylaniline → HCID 58409409、化合物

HRID 1026364ノート

反応式

HRID 1026364 の反応式
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]

参加物

5

反応物 3

HCID 32484DiisopropylanilineHCID 1401098-BromoquinolineHCID 23676156Sodium t-butoxide

生成物 1

HCID 58409409HCID 58409409、化合物収率 38%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a96733cda8244305ab238f8e8974ba3e
出典データセット
uspto-grants-2014_05
特許番号
US08729201B2

反応ノート

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