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Dimethyl Sulfoxide → Methyl 3-cyclohexyl-2-(2-formylphenyl)-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

HRID 1518260
Notes
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Reaction equation

HRID 1518260 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:30][C:31]#[CH:32])[C:18]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH2:39][OH:40])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC>C(Cl)Cl>[CH:11]1([C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:30][C:31]#[CH:32])[C:18]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH:39]=[O:40])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86637860HCID 86637860, compound

Product 1

HCID 86637861Methyl 3-cyclohexyl-2-(2-formylphenyl)-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

Oxalyl chloride (2.5 eq., 2M solution in DCM) was added at −70° C. under N2— atmosphere to a solution of DMSO (5 eq.) in anhydrous DCM and the mixture was stirred for 30 min; a solution of methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1-prop-2-yn-1-yl-1H-indole-6-carboxylate in DCM was then added and stirring was continued at the same temperature for 30 min. before NEt3 (8 eq.) was added. After stirring at 0° C. for 20 min. the mixture was diluted with DCM, washed with water, 1N HCl, saturated aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The obtained yellow solid was used in the next step without purification. MS (ES+): 400.5 (M+H+).

Workup

  1. stirringstirring
  2. additionwas added
  3. stirringAfter stirring at 0° C. for 20 min. the mixture
  4. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe obtained yellow solid was used in the next step without purification

Sources & evidence

ORD record
ord-26363c71b1c94870b3ab3d2700dfaeff
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232390B2

Reaction notes

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