Dimethyl Sulfoxide → Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 421966Notes

Reaction equation

HRID 421966 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]1([C:17]2[C:18]3[CH:19]=[CH:20][C:21]([C:37]([O:39][CH3:40])=[O:38])=[CH:22][C:23]=3[N:24]3[CH2:30][CH:29]([CH2:31][OH:32])[CH2:28][C:27]4[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=4[C:25]=23)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC>C(Cl)Cl>[CH:11]1([C:17]2[C:18]3[CH:19]=[CH:20][C:21]([C:37]([O:39][CH3:40])=[O:38])=[CH:22][C:23]=3[N:24]3[CH2:30][CH:29]([CH:31]=[O:32])[CH2:28][C:27]4[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=4[C:25]=23)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 16072734methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 86640311Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

DMSO (5 eq.) was dissolved in DCM and the solution was cooled to −78° C. At this temperature a 2M solution of oxalylchloride in DCM (2.5 eq.) was added slowly and the mixture was left stirring for 25 min at −78° C. A solution of methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (1 eq.) in DCM (0.09M) was added slowly at −78° C. and stirring was continued for 25 min at this temperature. Then NEt3 (8 eq.) was added and the resulting slurry was placed into an ice bath at 0° C. The mixture was stirred for 90 min, then diluted with DCM and extracted with water, HCl 1N, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. After evaporation of the solvent the product was obtained as a yellowish solid (quant.). (ES+) m/z 402 (M+H)+.

Workup

  1. waitthe mixture was left
  2. stirringstirring
  3. waitwas continued for 25 min at this temperature
  4. customthe resulting slurry was placed into an ice bath at 0° C
  5. stirringThe mixture was stirred for 90 min
  6. extractionextracted with water, HCl 1N, sat. aq. NaHCO3 and brine
  7. dry with materialAfter drying over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customAfter evaporation of the solvent the product
  10. customwas obtained as a yellowish solid (quant.)

Sources & evidence

ORD record
ord-5a8b09bda8fb45bba391ba78e43cab5e
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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