Diisopropylaniline → HCID 58409409, compound

HRID 1026364Notes

Reaction equation

HRID 1026364 reaction equation
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]

Participants

5

Reactant 3

HCID 32484DiisopropylanilineHCID 1401098-BromoquinolineHCID 23676156Sodium t-butoxide

Product 1

HCID 58409409HCID 58409409, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a96733cda8244305ab238f8e8974ba3e
Source dataset
uspto-grants-2014_05
Patent number
US08729201B2

Reaction notes

Loading…