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

HRID 1518252
Notes
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Reaction equation

HRID 1518252 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 left stirring 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 flash chromatography (PE:EtOAc, 9:1). After evaporation of the solvents the product was obtained as a yellow foam (88%). MS (ES+): 432.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-ee30a91f0d7d42a9a9762bdc2d6de347
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232390B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes