Potassium Carbonate → HCID 58114887, compound

HRID 1694528Notes

Reaction equation

HRID 1694528 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]([C:17]1[C:18]([O:30][CH3:31])=[C:19](B(O)O)[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)([CH3:16])([CH3:15])[CH3:14].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.C(COC)OC>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:19]1[CH:20]=[C:21]([C:23]([CH3:24])([CH3:26])[CH3:25])[CH:22]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:18]=1[O:30][CH3:31])[CH:11]=[CH:10]2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 15405941HCID 15405941, compoundHCID 459259512,8-Dibromoquinoline

Product 1

HCID 58114887HCID 58114887, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 2,8-dibromoquinoline (4.64 g, 16 mmol, prepared by the method of L. Mao et al., Tetrahedron Lett. 46 (2005) 8419), 3,5-di-tert-butyl-2-methoxyphenylboronic acid (4.3 g, 16 mmol), K2CO3 (5.6 g, 40 mmol), Pd(OAc)2 (0.08 g, 0.3 mmol), P(o-Tol)3 (0.2 g, 0.6 mmol), dimethoxyethane (40 mL) and water (10 mL) is refluxed for 8 h with 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/CH2Cl24:1). Yield: 5.2 g (77%).

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/CH2Cl24:1)

Sources & evidence

ORD record
ord-6e641ad5888a4c808590d9388ad7ae27
Source dataset
uspto-grants-2012_04
Patent number
US08158733B2

Reaction notes

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