Trifluoroacetic acid → HCID 67243509, compound

HRID 2423179Notes

Reaction equation

HRID 2423179 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][C:3]=1[OH:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:41][CH2:42][NH:43]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][C:3]=1[O:20][CH2:41][CH2:42][NH2:43]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 67241531HCID 67241531, compound2×

Product 1

HCID 67243509HCID 67243509, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To 6-fluoro-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 28, 3.0 g, 10 mmol), 1,1′-azobis(N,N (3.5 g, 21 mmol), triphenylphosphine (5.4 g, 21 mmol), tert-butyl N-(2-hydroxy-ethyl)carbamate (3.3 g, 21 mmol) and DCM (20 mL) were added. The mixture was heated at 150° C. for 20 minutes in a microwave heater. The reaction mixture was allowed to cool to room temperature and TFA (20 mL) was added. The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under reduced pressure and the crude material was filtered through a plug of silica gel using DCM as eluent. The solvent was removed under reduced pressure and the crude material was dissolved in ethyl acetate (10 mL) and the HCl salt of the title compound precipitated when 1 M HCl in diethylether (20 mL) was added. The solid was filtered off, dissolved in DCM (100 mL) and organic phase was washed with saturated aqueous NaHCO3 (40 mL) to give the title compound (2.0 g). MS m/z 335 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe crude material was filtered through a plug of silica gel
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe crude material was dissolved in ethyl acetate (10 mL)
  6. customthe HCl salt of the title compound precipitated when 1 M HCl in diethylether (20 mL)
  7. additionwas added
  8. filtrationThe solid was filtered off
  9. dissolutiondissolved in DCM (100 mL)
  10. washorganic phase was washed with saturated aqueous NaHCO3 (40 mL)

Sources & evidence

ORD record
ord-c8090542c211497aa1c237f4f659feee
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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