4-Toluenesulfonyl chloride → [4-Methoxy-2-(2-propen-1-yloxy)phenyl][2-methyl-1-[(4-methylphenyl)sulfonyl]-6-(trifluoromethoxy)-1H-indol-3-yl]methanone

HRID 1393333Notes

Reaction equation

HRID 1393333 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]([C:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:21][CH:22]=2)[NH:17][C:16]=1[CH3:29])=[O:14])[CH:2]=[CH2:3].[H-].[Na+].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>CN(C=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]([C:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:21][CH:22]=2)[N:17]([S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:16]=1[CH3:29])=[O:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 18438953HCID 18438953, compound

Product 1

HCID 18438952[4-Methoxy-2-(2-propen-1-yloxy)phenyl][2-methyl-1-[(4-methylphenyl)sulfonyl]-6-(trifluoromethoxy)-1H-indol-3-yl]methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6 (8.0 g, 20 mmol) in DMF (200 mL) was added NaH (1.5 eq). Mixture stirred for 15 min before addition of TsCl (1.5 eq, 5.6 g). After 1 hour, the reaction mixture was poured into ice water and extracted with CH2Cl2. The organic layer was washed with NH4Cl (2×), NaHCO3 and brine, then dried with Na2SO4 and concentrated. Purification via flash chromatography eluding with 20% EtOAc/hexanes afforded the product as a viscous yellow oil.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with NH4Cl (2×), NaHCO3 and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-cbb88c7f77f54dec9e5b0ba8afda8df7
Source dataset
uspto-grants-2008_03
Patent number
US07345085B2

Reaction notes

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