Hydrochloric Acid → HCID 67017196, compound

HRID 1020197Notes

Reaction equation

HRID 1020197 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH2:12]3)=[CH:5][CH:4]=1.[Br:20][C:21]1[S:25][C:24]([S:26](Cl)(=[O:28])=[O:27])=[CH:23][CH:22]=1.Cl>ClCCl>[Br:20][C:21]1[S:25][C:24]([S:26]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:8][CH:7]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)(=[O:28])=[O:27])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 20099580HCID 20099580, compound

Product 1

HCID 67017196HCID 67017196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.25 g commercially available 5-(4-Trifluoromethyl-phenyl)-2,3-dihydro-1H-indole were dissolved in 10 ml dichloromethane. Then 2.5 ml diidopropylethylamine were added. Then 1.37 g of commercially available 5-Bromo-thiophene-2-sulfonyl chloride dissolved in 5 ml dichloromethane were at 0° C. The mixture was stirred at room temperature for three hours. Then the mixture was poured on 100 ml 1M HCl and extracted five times with portions of 50 ml dichloromethane. The combined organic extracts were washed with 100 ml saturated NaHCO3 solution. The organic layer was then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by chromatography on silica gel to obtain 2.1 g of 1-(5-Bromo-thiophene-2-sulfonyl)-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole.

Workup

  1. additionThen 2.5 ml diidopropylethylamine were added
  2. customwere at 0° C
  3. extractionextracted five times with portions of 50 ml dichloromethane
  4. washThe combined organic extracts were washed with 100 ml saturated NaHCO3 solution
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customThe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a1d4fb93269d48c589017e10e1475c05
Source dataset
uspto-grants-2014_05
Patent number
US08716317B2

Reaction notes

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