Ammonia → (1S)-1-(2-{[7-(4-Fluorophenyl)quinolin-3-yl]sulfonyl}phenyl)ethanol

HRID 735331Notes

Reaction equation

HRID 735331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([S:18]([O-:20])=[O:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].I[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C@@H:29]([OH:31])[CH3:30].N>[Cu]I.CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([S:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C@@H:29]([OH:31])[CH3:30])(=[O:20])=[O:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10514669(1S)-1-(2-iodophenyl)ethanolHCID 68899227Sodium 7-(4-fluorophenyl)quinoline-3-sulfinate

Product 1

HCID 68901666(1S)-1-(2-{[7-(4-Fluorophenyl)quinolin-3-yl]sulfonyl}phenyl)ethanolYield 41.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium 7-(4-fluorophenyl)quinoline-3-sulfinate (2.52 g, 8.15 mmol), (1S)-1-(2-iodophenyl)ethanol (2.18 g, 8.79 mmol) and copper(I) iodide (4.69 g, 24.6 mmol) were weighed into a 3-neck round-bottomed flask. A nitrogen atmosphere was established by evacuation and back-filling with nitrogen. Dimethyl sulfoxide (50 mL) was added and the flask placed in an oil bath at 110° C. The reaction mixture was stirred at this temperature for 1 hour. The cooled reaction mixture was poured into concentrated ammonia solution (250 mL) and extracted with ethyl acetate (2×250 ml). The extracts were washed with brine (250 mL), combined, dried (MgSO4) and evaporated to an off-white solid. Recrystallisation from methanol gave the title compound (1.37 g, 41%). 1H NMR (500 MHz, DMSO-d6) δ 9.16 (2H, s), 8.41 (1H, d, J 8.6 Hz), 8.39 (1H, s), 8.19 (1H, dd, J 1.0, 8.0 Hz), 8.15 (1H, dd, J 1.7, 8.5 Hz), 7.99-7.97 (2H, m), 7.84 (1H, dd, J 1.0, 7.8 Hz), 7.78 (1H, t, J 7.1 Hz), 7.62-7.58 (1H, m), 7.39 (2H, t, J 8.8 Hz), 5.52-5.46 (1H, m), 5.29 (1H, d, J 3.9 Hz), 1.20 (3H, d, J 6.2 Hz); m/z (ES+) 408 [MH+].

Workup

  1. customthe flask placed in an oil bath at 110° C
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (2×250 ml)
  4. washThe extracts were washed with brine (250 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated to an off-white solid
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-4ceafa0073164f4492c335f2ebf4d6e2
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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