Potassium Carbonate → HCID 59326516, compound

HRID 238632Notes

Reaction equation

HRID 238632 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[C:5]2[SH:16].F[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[C:5]2[S:16][C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 59326575HCID 59326575, compound

Product 1

HCID 59326516HCID 59326516, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (6-fluoro-4-mercapto-naphthalen-2-yl)-acetic acid (30 mg, 0.127 mmol) in N,N-dimethylformamide (2 mL), was added 1-fluoro-4-methanesulfonyl-benzene (43.4 mg, 0.25 mmol) and potassium carbonate (35 mg, 0.25 mmol) under a nitrogen atmosphere. After being heated under microwave conditions (100° C., 30 minutes), the resulting mixture was diluted with water (10 mL) and extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-20% methanol in dichloromethane) to afford [6-fluoro-4-(4-methanesulfonyl-phenylsulfanyl)-naphthalen-2-yl]-acetic acid (37.0 mg, 74.6%) as an off-white powder. 1H NMR (400 MHz, CDCl3) δ ppm 7.86-7.93 (m, 4H), 7.69-7.74 (m, 2H), 7.34 (td, J=8.53, 2.65 Hz, 1H), 7.08-7.15 (m, 2H), 3.85 (s, 2H), 3.01 (s, 3H); MS cald. for C19H15FO4S2 390, obsd. (ESI+) [(M+H)+] 391.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (0-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-93f89aadc0eb430a9dc6ee4e60538515
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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