Sodium Carbonate → HCID 58305606, compound

HRID 2362249Notes

Reaction equation

HRID 2362249 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[N:8]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[CH3:20])[CH:9]=[CH:10][CH:11]=1.[C:21](=O)([O-])[O-:22].[Na+].[Na+]>CN(C=O)C>[Br:6][C:7]1[N:8]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[CH3:20])[C:9]([CH:21]=[O:22])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 58305731HCID 58305731, compound

Product 1

HCID 58305606HCID 58305606, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DMF (0.1 mL) was added to phosphorus oxychloride (0.5 mL, 5.2 mmol) at 0° C., and the mixture was stirred at room temperature for 1.5 h. At 0° C., a solution of compound 50B (100 mg. 0.36 mmol) in DMF (2 mL) was added, and the resultant mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice-water, adjusted to pH=8 with saturated aqueous sodium carbonate solution, and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with brine (20 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC to afford 50C (60 mg, yield 58%).

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe combined organic layers were washed with brine (20 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-84d6441963eb483bac1ca471968f8cb6
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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