Cesium carbonate → HCID 67070140, compound

HRID 2390829Notes

Reaction equation

HRID 2390829 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[C:13]([O:18]C)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[Na+].[C:21]1([S:27]([O-:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:21]1([S:27]([C:2]2[CH:3]=[C:4]([C:12]3[C:13](=[O:18])[NH:14][CH:15]=[CH:16][CH:17]=3)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 67070084HCID 67070084, compound

Product 1

HCID 67070140HCID 67070140, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

step 2—A mixture of 122 (150 mg, 0.469 mmol), benzene sulfinic acid sodium salt (94 mg, 0.573 mmol), Pd2(dba)3 (45 mg, 0.049 mmol), 4,5-bis-(diphenylphosphine)-9,9-dimethylxanthine (56 mg, 0.097 mmol, xantphos, CASRN 161265-03-8), tetrabutylammonium chloride (156 mg, 0.561 mmol), and Cs2CO3 (234 mg, 0.718 mmol) in a Schlenk flask was purged with argon 3 times before toluene (5 mL) was added. The reaction mixture was heated at 120° C. under an argon atmosphere overnight. The reaction mixture was cooled to RT, diluted with EtOAc and water. The organic layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 column chromatography eluting with an EtOAc/hexane gradient (10 to 20% EtOAc) to afford 0.119 g (67%) of I-107 as a light brown oil.

Workup

  1. customwas purged with argon 3 times before toluene (5 mL)
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to RT
  4. additiondiluted with EtOAc and water
  5. washThe organic layer was washed sequentially with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by SiO2 column chromatography
  10. washeluting with an EtOAc/hexane gradient (10 to 20% EtOAc)
  11. customto afford 0.119 g (67%) of I-107 as a light brown oil

Sources & evidence

ORD record
ord-c1271632a6144c44865346f2f8f87bf3
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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