Sodium Bicarbonate → HCID 58958219, compound

HRID 914982Notes

Reaction equation

HRID 914982 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[CH:3]=[CH:4][CH:5]=[C:6]([CH:20]=[O:23])[CH:7]=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 58958219HCID 58958219, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 71 (294 mg, 0.94 mmol) in toluene (9.6 mL) under N2 were sequentially added saturated NaHCO3 (aq. 3.8 mL), a solution of 72 (199 mg, 1.33 mmol) in EtOH (6.7 mL), and PdCl2(Ph3P)3 (32 mg, 0.046 mmol). The reaction was heated at 80° C. for 21 hours before it was allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate (40 mL) and washed with water (15 mL), brine (15 mL). The ethyl acetate extracts were dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on silica gel (dichloromethane to 20:1 dichloromethane/methanol) to give 73 as a yellow solid (219 mg, 68.9%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate (40 mL)
  3. washwashed with water (15 mL), brine (15 mL)
  4. dry with materialThe ethyl acetate extracts were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (dichloromethane to 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-75dbbd78552e497ba408480cec873057
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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