Hydrochloric Acid → 3-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde

HRID 242844Notes

Reaction equation

HRID 242844 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:18]=2[CH2:36][OH:37])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(Cl)Cl.C(N(CC)CC)C>[C:11]1([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)(=[O:27])=[O:28])[C:18]=2[CH:36]=[O:37])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 68156952[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol

Product 1

HCID 547518363-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of oxalyl chloride (1.37 g, 10.8 mmol) in DCM (30 mL) cooled to −78° C. and under a nitrogen atmosphere was added DMSO (1.50 mL, 21.6 mmol). After stirring for 10 min at −78° C., a solution of [3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol (2.27 g, 6.01 mmol) in DCM (20 mL) was added and stirring was continued for 1.5 h. Triethylamine was then added and, after stirring for 10 min at −78° C., the mixture was slowly warmed to RT. The reaction mixture was then poured into a 1.0M aq HCl solution and extracted with DCM (×3). The combined organic layers were washed with water, then with brine, dried (Na2SO4) and concentrated in vacuo affording 3-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carbaldehyde as a gum which then solidified on standing to give an off-white solid (2.26 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 10.22 (1H, s), 8.31 (1H, d, J=8.56 Hz), 7.86-7.81 (2H, m), 7.60-7.41 (7H, m), 7.33-7.21 (3H, m), 2.37 (3H, s).

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 h
  3. stirringafter stirring for 10 min at −78° C.
  4. temperaturethe mixture was slowly warmed to RT
  5. extractionextracted with DCM (×3)
  6. washThe combined organic layers were washed with water
  7. dry with materialwith brine, dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53d8a54a81994d46a50c85d67b9518cc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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