Toluene → HCID 9818529, compound

HRID 1167196Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([CH:17]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=O)=O.[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:27]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([CH:17]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

0.1 g (0.254 mmol) of 2-trifluoromethanesulfonyloxy-8-(1-diethylamino-2-hydroxyethyl)quinoline, 3 ml of toluene, 62 mg (0.51 mmol) of of phenylboronic acid, 53 mg (0.38 mmol) of potassium carbonate and 17.6 mg (0.0152 mmol) of tetrakis(triphenylphosphine)palladium are placed in a 20 ml three-necked flask. The mixture is heated with an oil bath at 90° C. for 2 h and 10 ml of water are added. Extraction is carried out with ethyl acetate and the organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: dichloromethane/methanol 95/5) to provide 40 mg of 2-phenyl-8-(1-diethylamino-2-hydroxyethyl)quinoline in the form of a colorless oil. (Yield: 49%)

Workup

extractionExtraction
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue is purified by silica chromatographic column (eluent: dichloromethane/methanol 95/5)

Sources & evidence

ORD record: ord-cbe8ffaae6f94161ad3f6d58f2fff70d
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617336B1

Reaction notes

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