HCID 13836887, compound → HCID 19600424, compound

HRID 609740Notes

Reaction equation

HRID 609740 reaction equation
C([Sn](CCCC)(CCCC)[CH:6]1[CH2:11][CH2:10][CH:9]=[CH:8][O:7]1)CCC.Br[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:25]=[C:24]2[CH:38]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39]1>C1(C)C=CC=CC=1>[O:7]1[CH:8]=[CH:9][CH2:10][CH2:11][CH:6]1[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:25]=[C:24]2[CH:38]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39]1

Participants

4

Reactant 2

HCID 13836887HCID 13836887, compoundHCID 19600465HCID 19600465, compound

Product 1

HCID 19600424HCID 19600424, compoundYield 566.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-tributylstannyl-2,3-dihydropyran (Example 6, 0.41 g, 0.11 mmol) in anhydrous toluene (15 mL) was added 5-bromo-3-(N-methylpyrrolidin-3-yl)-1-benzoylindole (Example 5b, 0.280 g, 0.729 mmol) and Pd[PPh3 ]4 (0.09 g, 0.076 mmol). The mixture was heated to reflux for 6.5 hours, cooled, filtered through celite and concentrated by reduced pressure. The crude product was purified by column chromatography [95:5 CH2Cl2 : NH3 (2M in MeOH)] to yield the title compound (0.241 g, 85%) as a yellow oil; HRMS-FAB+ for C25H26N2O2 ; calc. MH+ :387.2072; found MH+ :387.2092.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6.5 hours
  3. temperaturecooled
  4. filtrationfiltered through celite and
  5. concentrationconcentrated by reduced pressure
  6. customThe crude product was purified by column chromatography [95:5 CH2Cl2 : NH3 (2M in MeOH)]

Sources & evidence

ORD record
ord-3ca4ed7045e64df28af3388de12e93cc
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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