HCID 86688721, compound → HCID 86688720, compound

HRID 1423379Notes

Reaction equation

HRID 1423379 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:22][CH2:23][CH:24]([OH:29])C(F)(F)F)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC1C=CC(S(NC2CCC3C(=CC=CC=3CCCO)C2)(=O)=O)=CC=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:22][CH2:23][CH:24]=[O:29])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 86688721HCID 86688721, compoundHCID 86688722HCID 86688722, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86688720HCID 86688720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-N-(5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide, designated as 23 in FIG. 7, was prepared as follows. A mixture of 4-fluoro-N-(5-(3-hydroxypropyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide (70 mg, 0.19 mmol) and pyridinium chlorochromate (60 mg, 0.28 mmol) in anhydrous dichloromethane (3 mL) was stirred at room temperature for 1 hour. The reaction mixture was filtered through a pad of celite, and the solvent was evaporated. The residue was purified by a short silica gel column chromatography using ethyl acetate-hexanes 2:3 as eluent to give 4-fluoro-N-(5-(3-oxopropyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide (20) that was dissolved in anhydrous tetrahydrofuran (1 mL) and cooled to 0 C. Tetrabutylammoniumfluoride in THF (5 μL, 1 M, 0.004 mmol) was added followed by trifluoromethyl trimethylsilane (30 mg, 33 μL, 0.21 mmol). The reaction was warmed to room temperature and stirred overnight. Hydrochloric acid (1 M, 1.5 mL) was added and stirring continued at room temperature for 1.5 hour. The aqueous layer was extracted with dichloromethane, dried over magnesium sulfate and concentrated to dryness. Silica gel chromatography (30% ethyl acetate in hexanes) gave the purified product as colorless oil. Yield: 13%.

Workup

  1. customwas prepared
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customthe solvent was evaporated
  4. customThe residue was purified by a short silica gel column chromatography

Sources & evidence

ORD record
ord-ccab7f8f4ed54468b983d481c9dc67bb
Source dataset
uspto-grants-2015_01
Patent number
US08927586B2

Reaction notes

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