Sodium Carbonate → HCID 58305576, compound

HRID 2362250Notes

Reaction equation

HRID 2362250 reaction equation
Br[C:2]1[N:3]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[CH3:17])[C:4]([CH:7]=[O:8])=[CH:5][CH:6]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH:7]([C:4]1[N:3]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[CH3:17])[C:2]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:6][CH:5]=1)=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 58305606HCID 58305606, compound

Product 1

HCID 58305576HCID 58305576, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of compound 50C (24 mg, 0.083 mmol), compound 4-methoxyphenylboronic acid (15.2 mg, 0.1 mmol) and sodium carbonate (17.6 mg, 0.166 mmol) in a mixture of DME (5 mL) and water (1 mL) was degassed, and [11′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (96 mg, 0.008 mmol) was added. The reaction mixture was heated at 90° C. for 10 hours, poured into water, and extracted with ethyl acetate (10 mL×3). The combine organic layers were washed with brine (20 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrate under reduced pressure, and purified by preparative TLC to afford the compound 50D (15 mg, 57%).

Workup

  1. customwas degassed
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. washThe combine organic layers were washed with brine (20 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrate under reduced pressure
  7. custompurified by preparative TLC

Sources & evidence

ORD record
ord-d52894b33bce49849ea32053c4dec7c3
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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