Triethylamine → HCID 9842227, compound

HRID 1441056Notes

Reaction equation

HRID 1441056 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([Sn](CCCC)(CCCC)CCCC)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.C(N(CC)CC)C.Br[C:54]1[CH:55]=[C:56]2[C:60](=[CH:61][CH:62]=1)[NH:59][CH:58]=[C:57]2[CH2:63][C@H:64]1[CH2:68][CH2:67][CH2:66][N:65]1[CH3:69]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:69][N:65]1[CH2:66][CH2:67][CH2:68][C@@H:64]1[CH2:63][C:57]1[C:56]2[C:60](=[CH:61][CH:62]=[C:54]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=3)[CH:55]=2)[NH:59][CH:58]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indoleHCID 22502783HCID 22502783, compound

Product 1

HCID 9842227HCID 9842227, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-methylsulphonylphenyltri-n-butylstannane (see Preparation 15) (680 mg, 1.53 mmol) tri-o-tolyphosphine (120 mg, 0,394 mmol), palladium (II) acetate (15 mg, 0.067 mmol), triethylamine (0.40 ml, 2.87 mmol) and 5-bromo-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole (400 mg, 1.36 mmol) (see Preparation 36) in anhydrous acetonitrile (5 ml) was heated under reflux, under nitrogen, for 18 hours. The reaction mixture was then evaporated under reduced pressure and dichloromethane (25 ml) was added. The resultant solution was washed with aqueous sodium carbonate, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/diethylamine (98:2) to afford, after combination and evaporation of the appropriate fractions, the title compound as a white foam, (189 mg). Found: C,68.17; H,6.81; N,7.53; C21H24N2O2S.1/20 CH2Cl2 requires: C,67.83; H,6.51; N,7.52%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, under nitrogen, for 18 hours
  3. customThe reaction mixture was then evaporated under reduced pressure and dichloromethane (25 ml)
  4. additionwas added
  5. washThe resultant solution was washed with aqueous sodium carbonate
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate/diethylamine (98:2)
  10. customto afford
  11. customafter combination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-37a6feab69b84ce99f1fe057cbd60b83
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

Loading…