Dimethyl Sulfoxide → methyl 1-allyl-3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate

HRID 1669433Notes

Reaction equation

HRID 1669433 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[CH2:41][OH:42])[CH:12]=[CH2:13].CCN(CC)CC>C(Cl)Cl>[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[CH:41]=[O:42])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67345867methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate

Product 1

HCID 86627900methyl 1-allyl-3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

DMSO (5 eq) was dissolved in DCM and the solution was cooled to −78° C. To the stirred solution oxalylchloride (2.5 eq) was added and the mixture was left stirring for 30 min. A solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate (1 eq) in DCM (0.25M solution) was added and the mixture was stirred for 30 min at −78° C. Et3N (8 eq) was added and the mixture was allowed to warm to 0° C. At this temperature stirring was continued for 2 h, and then stirring was continued at RT overnight. The mixture was diluted with DCM, and then washed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was purified by FC (PE:EtOAc, 9:1). After evaporation of the solvents the product was obtained as a yellow foam (88%). (ES+): m/z 432.1 (M+H)+.

Workup

  1. waitthe mixture was left
  2. stirringthe mixture was stirred for 30 min at −78° C
  3. temperatureto warm to 0° C
  4. stirringAt this temperature stirring
  5. waitwas continued for 2 h
  6. stirringstirring
  7. waitwas continued at RT overnight
  8. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine
  9. dry with materialAfter drying over Na2SO4 all volatiles
  10. customwere evaporated in vacuo
  11. customThe residual material was purified by FC (PE:EtOAc, 9:1)
  12. customAfter evaporation of the solvents the product

Sources & evidence

ORD record
ord-25982367ebba4af78c1c9304ea741b44
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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