4-(Methylsulfonyl)aniline → HCID 58482986, compound

HRID 238963Notes

Reaction equation

HRID 238963 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[C:28]([F:31])([F:30])[F:29])[C:7]=1[CH3:32])=[O:5])C.[CH3:33][S:34]([C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)(=[O:36])=[O:35].C[Al](C)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][CH2:12][CH2:11][C:9]1[N:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[C:28]([F:29])([F:31])[F:30])[C:7]([CH3:32])=[C:6]([C:4]([NH:41][C:40]2[CH:39]=[CH:38][C:37]([S:34]([CH3:33])(=[O:36])=[O:35])=[CH:43][CH:42]=2)=[O:5])[CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 796174-(Methylsulfonyl)anilineHCID 16682925TrimethylaluminumHCID 67376475HCID 67376475, compound

Product 1

HCID 58482986HCID 58482986, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 5-[2-(benzyloxy)ethyl]-1-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (332 mg, 0.74 mmol) and 4-(methylsulfonyl)aniline (133 mg, 0.78 mmol) in toluene (3 mL), Me3Al (0.41 mL, 0.74 mmol, 1.8 M solution in toluene) was added under N2 atmosphere at room temperature and stirred at 110° C. for 30 min. After the completion of the reaction, it was quenched with 1N HCl, and extracted with AcOEt. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated, and the residue was purified over silica gel (AcOEt/n-hexane, 2:3 v/v) to give the atropisomeric mixture of the title compound (220 mg, 52%) as an oil.

Workup

  1. additionwas added under N2 atmosphere at room temperature
  2. customAfter the completion of the reaction, it
  3. customwas quenched with 1N HCl
  4. extractionextracted with AcOEt
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customthe residue was purified over silica gel (AcOEt/n-hexane, 2:3 v/v)
  9. customto give

Sources & evidence

ORD record
ord-c002edf752fb4b9f9eaae0207f6ba31e
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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