Potassium Carbonate → HCID 58114889, compound

HRID 2266928Notes

Reaction equation

HRID 2266928 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC([O-])=O.CC([O-])=O.[Pd+2].O.COCCOC>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:21]1[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=1)[CH:11]=[CH:10]2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2545321-Naphthaleneboronic acidHCID 459259512,8-Dibromoquinoline

Product 1

HCID 58114889HCID 58114889, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2,8-dibromoquinoline (6.0 g, 21 mmol, prepared by the method of L. Mao et al., Tetrahedron Lett. 46 (2005) 8419), 1-naphthylboronic acid (4.1 g, 24 mmol), K2CO3 (6.6 g, 48 mmol), Pd(OAc)2 (0.1 g, 0.4 mmol), P(o-Tol)3 (0.25 g, 0.8 mmol), DME (50 mL) and water (10 mL) is refluxed for 6 h under stirring in an argon atmosphere. The mixture is then poured into water and extracted with CHCl3 (3×50 mL). The combined organic phase is washed with water and brine, and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/benzene 1:1). Yield of red purple oil: 4.1 g (57%).

Workup

  1. customprepared by the method of L
  2. extractionextracted with CHCl3 (3×50 mL)
  3. washThe combined organic phase is washed with water and brine
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography (silica gel 40, hexane/benzene 1:1)

Sources & evidence

ORD record
ord-3f01200e94e04784a7c399fce907cea2
Source dataset
uspto-grants-2010_12
Patent number
US07858718B1

Reaction notes

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