Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate → 2-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}phenyl)pyrazine

HRID 735339Notes

Reaction equation

HRID 735339 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([O-:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[Na+].I[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[N:33][CH:32]=[CH:31][N:30]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:34]=[N:33][CH:32]=[CH:31][N:30]=2)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinateHCID 689016222-(2-Iodophenyl)pyrazine

Product 1

HCID 688994072-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}phenyl)pyrazineYield 39%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (145 mg, 0.47 mmol) and 2-(2-iodophenyl)pyrazine (0.11 g, 0.46 mmol) according to the methods of Example 6 Step 4. Purification by flash column chromatography eluting with a 10-60% ethyl acetate/isohexane gradient gave 2-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)pyrazine (79 mg, 38%). 1H NMR (500 MHz, CDCl3) δ 8.77 (1H, d, J=1.2 Hz), 8.51 (1H, d, J=2.4 Hz), 8.44-8.38 (1H, m), 8.28-8.23 (1H, m), 8.03 (1H, s), 7.98 (1H, s), 7.87 (2H, t, J=8.8 Hz), 7.79 (1H, dd, J=1.6, 8.5 Hz), 7.74-7.62 (4H, m), 7.56 (1H, dd, J=1.7, 8.6 Hz), 7.42-7.35 (1H, m), 7.23-7.15 (2H, m); m/z (ES+) 441 [MH+].

Workup

  1. customPurification by flash column chromatography
  2. washeluting with a 10-60% ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-d0ed008656b3451995504c74f1c99553
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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