(2aS,4R)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole → HCID 86747034, compound

HRID 484166Notes

Reaction equation

HRID 484166 reaction equation
C([N:9]1[C:17]2[CH:16]=[CH:15][C:14](I)=[C:13]3[CH2:19][C@H:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:21][C@@H:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.C[SiH](C)C.[CH:33]#[CH:34].C[Sn](C)C>C1(C)C=CC=CC=1>[C:33]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][CH2:10][C@H:11]3[CH2:21][C@@H:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:19][C:13]=1[C:12]=23)#[CH:34]

Participants

4

Reactant 2

HCID 18652842(2aS,4R)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indoleHCID 131718028HCID 131718028, compound

Product 1

HCID 86747034HCID 86747034, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-benzoyl-(2aS,4R)-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (100 mg, 0.205 mmol) and trimethyltin acetylene trimethylsilane (272 mg, 1.0 mmol, 3 eq) was dissolved in anhydrous toluene (5 mL), to which was then added tetrakis-triphenylphosphine palladium (20 mg, 0.017 mmol, 0.05 eq). The resulting light yellow solution was brought to reflux under N2 atmosphere. After 4 hr, the reaction mixture was cooled to room temperature, filtered and concentrated to dryness. The residue was chromatographed over silica gel with hexanes:ethyl acetate (1:1) to afford the desired product (79 mg, 84%). This material was dissolved in a 1N solution (5 mL) of tetrabutylammonium fluoride in THF, and stirred at room temperature overnight (12 h). The solution was diluted with EtOAc (10 mL) and rinsed successively with H2O (3×10 mL), brine (10 mL) and dried over Na2SO4. The residue was chromatographed over silica gel with hexanes:ethyl acetate (1:1) to afford a mixture of the 1-benzoyl (61%) and the N-deprotected indoline (33%).

Workup

  1. temperatureto reflux under N2 atmosphere
  2. filtrationfiltered
  3. concentrationconcentrated to dryness
  4. customThe residue was chromatographed over silica gel with hexanes:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-2cc39d58b9814799a731baf39aa6f6cf
Source dataset
uspto-grants-1993_07
Patent number
US05229410

Reaction notes

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