1,2-Dimethoxyethane → HCID 66712644, compound

HRID 1866360Notes

Reaction equation

HRID 1866360 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-:23].[Cs+].[Cs+].C(=O)(O)[O-].[Na+].[CH3:33][O:34][CH2:35][CH2:36]OC>>[CH3:33][O:34][C:35](=[O:23])[CH2:36][N:7]1[C:5](=[O:6])[C:4]2[C:3](=[CH:2][CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[C:8]1=[O:9]

Participants

6

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 226073074-Bromo-1H-isoindole-1,3(2H)-dione

Product 1

HCID 66712644HCID 66712644, compound

Conditions

Temperature
65 °C

Procedure

6.0 g of the above bromo-phthalimide product was dissolved in 70 ml of ethylene glycol dimethyl ether. To the solution was added 3.7 g of phenyl boronic acid, 13 g cesium carbonate, and 2 g tetakis(triphenylphosphine)palladium(0). The mixture was stirred under a nitrogen atmosphere at 65° C. for 48 h. The resultant mixture was poured into 250 ml of half saturated aqueous sodium bicarbonate solution, and then extracted with 200 ml portions of ethyl acetate three times. The combined organic fractions were successively washed with 200 ml of water, saturated sodium bicarbonate, and brine solutions, and then dried over sodium sulfate. The solution was concentrated to a residue (11 g), which was purified by chromatography on silica gel using a gradient of 0 to 25% ethyl acetate in hexanes to elute the desired product. 1.1 g of purified product was obtained; MS (+): m/z 296.02 (M+1)

Workup

  1. extractionextracted with 200 ml portions of ethyl acetate three times
  2. washThe combined organic fractions were successively washed with 200 ml of water, saturated sodium bicarbonate, and brine solutions
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solution was concentrated to a residue (11 g), which
  5. customwas purified by chromatography on silica gel using a gradient of 0 to 25% ethyl acetate in hexanes
  6. washto elute the desired product

Sources & evidence

ORD record
ord-ccec1101d14a42e59fa9222ae8e02a3f
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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