Triethylamine → HCID 59599679, compound

HRID 2266646Notes

Reaction equation

HRID 2266646 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][NH:1]2)=[CH:6][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 939807-Quinolinol, 1,2,3,4-tetrahydro-

Product 1

HCID 59599679HCID 59599679, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.15 g (1.01 mmol) 1,2,3,4-tetrahydro-quinolin-7-ol in 10 ml dichloromethane were added 0.19 g (1.56 mmol) phenylboronic acid, 0.27 g (1.49 mmol) copper(II) acetate, a spatula end of 4 Å molecular sieves and 0.64 ml (5.03 mmol) triethylamine. The reaction mixture was stirred at room temperature for 72 hours and then filtered through celite, washing with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 15 mg (7%) of the title compound as a light yellow oil. MS (ISP): 226.3 ([M+H]+).

Workup

  1. filtrationfiltered through celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-ce204272998546009674e090224a06ef
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

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