Sodium Bicarbonate → 6-(Benzyloxy)-2-(2,6-dichlorophenyl)quinoline

HRID 1869797Notes

Reaction equation

HRID 1869797 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14](Cl)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1B(O)O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CO.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>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:22]1[C:21]([Cl:20])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:27])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343322,6-Dichlorobenzeneboronic acidHCID 112194246-(Benzyloxy)-2-chloroquinoline

Product 1

HCID 579876386-(Benzyloxy)-2-(2,6-dichlorophenyl)quinolineYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3 g of 6-(benzyloxy)-2-chloroquinoline 12 in toluene (294 ml) is added Pd(PPh3)4 (1 g). After 30 minutes, a solution of 2,6-dichlorophenylboronic acid (4.22 g) in methanol (186 ml) and 120 ml of a saturated aqueous solution of NaHCO3 is added. The reaction is heated under reflux for 4 h. After evaporation, the aqueous phase is extracted with AcOEt (3×20 ml). The organic phases are washed with brine, dried over MgSO4 and evaporated to dryness. The residue is purified over silica gel using AcOEt/petroleum ether 5/95 then 10/90 as eluent to give 6-(benzyloxy)-2-(2,6-dichlorophenyl)quinoline 19 as an oil.

Workup

  1. temperatureThe reaction is heated
  2. temperatureunder reflux for 4 h
  3. customAfter evaporation
  4. extractionthe aqueous phase is extracted with AcOEt (3×20 ml)
  5. washThe organic phases are washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue is purified over silica gel

Sources & evidence

ORD record
ord-bc7f458e27014b8b84658e9ded040484
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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