5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole → 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

HRID 609732

Reaction equation

HRID 609732 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[C:5]2[CH2:19][CH2:20][N:21]([CH3:23])[CH3:22].C([Sn](CCCC)(CCCC)[CH:29]1[CH:34]=[CH:33][O:32][CH2:31][CH2:30]1)CCC>C1(C)C=CC=CC=1>[O:32]1[CH:31]=[CH:30][CH:29]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[C:5]3[CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 196004435-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindoleHCID 196004524-Tributylstannyl-3,4-dihydropyran

Product 1

HCID 196004485-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindoleYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (Example 5a, 180 mg 0.48 mmol), 4-tributylstannyl-3,4-dihydropyran (180 mg, 0.48 mmol) and tetrakistriphenyphosphine palladium (118 mg, 0.1 mmol) in toluene (3 mL) was stirred at 100-110° C. A second portion of catalyst was added after 1 h and heating was continued overnight. After removal of the solvent in vacuo, flash chromatography on silica gel (2-6% 2M methanolic ammonia in dichloromethane) yielded 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (30.5 mg, 17%).

Workup

  1. additionA second portion of catalyst was added after 1 h
  2. temperatureheating
  3. customAfter removal of the solvent in vacuo, flash chromatography on silica gel (2-6% 2M methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-1f04ef2904a540abb5f21fe0815090e6
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Linked notes

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