Benzenesulfonyl chloride → HCID 57473900, compound

HRID 1868406Notes

Reaction equation

HRID 1868406 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.Cl>[F:16][C:2]([F:1])([F:15])[CH:3]([NH:14][S:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:25])=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 57473900HCID 57473900, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 40 mg (0.18 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 30 μL (0.23 mmol) of benzenesulfonyl chloride in 1 mL of pyridine was warmed at 45° C. The reaction was monitored by TLC (ethyl acetate-hexanes (25:75)) indicating a new less polar product compared to amine. The mixture stirred for 18 hours at 45° C. and over the weekend at room temperature. The mixture was diluted with 7 mL of 1 N aqueous HCl and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, and three 5 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed onto silica gel and chromatographed on silica gel using dichloromethane-hexanes (gradient 50-100%). The material from the column solidified from ether-hexanes to afford 44 mg (68%) of the title compound as an white solid, m.p. 121° C.-123° C., MS: m/z 367.08 (M−).

Workup

  1. extractionextracted with three 7 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, and three 5 mL portions of saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ebcaaa3207234c01ba5470c7ed44a590
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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