Sodium Bicarbonate → HCID 59648455, compound

HRID 914993Notes

Reaction equation

HRID 914993 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([CH3:19])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:20]([O-:23])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCO>[CH3:19][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([C:2]3[C:7]([CH:20]=[O:23])=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:7]=[CH:6][CH:5]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 798200HCID 798200, compound

Product 1

HCID 59648455HCID 59648455, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 71 (411 mg, 1.31 mmol) in toluene (12.8 mL) under N2 were sequentially added saturated NaHCO3 (aq. 0.5 mL), a solution of 99 (303 mg, 2.02 mmol) in EtOH (8.9 mL), and PdCl2(Ph3P)3 (52 mg, 0.07 mmol). The reaction was heated at 80° C. for 41 hours before it was allowed to cool to room temperature and extracted with ethyl acetate (50 mL). The ethyl acetate extracts were washed with water (30 mL), brine (30 mL), dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (dichloromethane to 20:1 dichloromethane/methanol) to give 100 as a yellow solid (166 mg, 37.4%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe ethyl acetate extracts were washed with water (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (dichloromethane to 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-a149ecd2c010420b8404d3a3f2826d5c
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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