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Tert-Butanesulfinamide → (+/-)-tert-Butyl 4-(1-((tert-butylsulfinyl)imino)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2173954
Notes
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Reaction equation

HRID 2173954 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:20](=O)[C:21]([F:24])([F:23])[F:22])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6]2.[CH3:26][C:27]([S:30]([NH2:32])=[O:31])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[C:27]([S:30]([N:32]=[C:20]([C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:10]([CH3:12])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[C:21]([F:22])([F:24])[F:23])=[O:31])([CH3:29])([CH3:28])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 86701516tert-Butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoroacetyl)-1H-indole-1-carboxylate

Product 1

HCID 86701517(+/-)-tert-Butyl 4-(1-((tert-butylsulfinyl)imino)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent
HCID 8857
Ethyl Acetate
Solvent
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoroacetyl)-1H-indole-1-carboxylate (0.45 g, 1.26 mmol) and 2-methyl-2-propanesulfinamide (0.46 g, 3.78 mmol) in toluene (12.6 mL), Zr(O-t-Bu)4 (2.52 mL, 6.30 mmol) was added at room temperature, and the reaction was heated to 100° C. After 15 minutes the reaction mixture was cooled to room temperature and diluted with EtOAc and sat. aq. brine. The resulting mixture was filtered and the layers separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 461.3 (M+H).

Workup

  1. temperatureAfter 15 minutes the reaction mixture was cooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

Sources & evidence

ORD record
ord-ff8fdda6dc494e5cb2e5304e48998e3c
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056874B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes