Sodium Carbonate → HCID 86701175, compound

HRID 572135Notes

Reaction equation

HRID 572135 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].C(B(CC)[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)C>COCCOC.O>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 6909582-Chloro-3-quinolinecarboxaldehyde

Product 1

HCID 86701175HCID 86701175, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloroquinoline-3-carbaldehyde (5.0 g, 26.1 mmol), Na2CO3 (4.15 g, 39.1 mmol) and diethyl(3-pyridyl)borane (4.22 g, 28.7 mmol) in DME (100 mL) and water (30 mL) was degassed by bubbling nitrogen gas through it for 5 minutes. Tetrakis-(triphenylphosphine)palladium(0) (0.30 g, 0.261 mmol) was added and the mixture was heated at 90° C. for 5 h. The mixture was allowed to cool to room temperature. The resultant precipitate was filtered off and washed with water (5×50 mL) and diethyl ether (5×50 mL) to give the title compound (4.3 g, 70%) as a pale green solid. LCMS (ES+) 235 (M+H)+, RT 1.53 minutes.

Workup

  1. customwas degassed
  2. customby bubbling nitrogen gas through it for 5 minutes
  3. temperatureto cool to room temperature
  4. filtrationThe resultant precipitate was filtered off
  5. washwashed with water (5×50 mL) and diethyl ether (5×50 mL)

Sources & evidence

ORD record
ord-0375bc43e7da4b43a646fc5642f3dc38
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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