Sodium Carbonate → HCID 86701176, compound

HRID 572136Notes

Reaction equation

HRID 572136 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]=1>O1CCOCC1.O.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>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:25]1[CH:24]=[N:23][C:22]([Cl:21])=[CH:27][CH:26]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 38450342-Chloropyridine-5-boronic acidHCID 149171252,8-Dichloro-quinoline-3-carbaldehyde

Product 1

HCID 86701176HCID 86701176, compoundYield 123.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (2.6 g, 11.5 mmol), Na2CO3 (1.83 g, 17.3 mmol) and 2-chloropyridin-5-ylboronic acid (1.81 g, 11.5 mmol) in 1,4-dioxane (40 mL) and water (20 mL) was degassed by bubbling nitrogen gas through it for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) was added and the mixture was heated at 90° C. for 16 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 tan solid.

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-ade8af467b1940b192a31e74ae095705
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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