Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate → (2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)(1H-imidazol-2-yl)methanol

HRID 735343Notes

Reaction equation

HRID 735343 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+].[NH:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1I)[OH:28]>>[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:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH:27]([C:23]2[NH:24][CH:25]=[CH:26][N:22]=2)[OH:28])(=[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 689021281H-imidazol-2-yl(2-iodophenyl)methanol

Product 1

HCID 68899402(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)(1H-imidazol-2-yl)methanolYield 51.7%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (193 mg, 0.62 mmol) and 1H-imidazol-2-yl(2-iodophenyl)methanol (171 mg, 0.57 mmol) according to the method of Example 6 Step 4. Purification by flash column chromatography eluting with ethyl acetate gave solid (2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)(1H-imidazol-2-yl)methanol (135 mg, 51%). 1H NMR (500 MHz, d6-DMSO) δ 11.94 (1H, s), 8.54 (1H, s), 8.30 (1H, s), 8.19 (1H, d, J=8.6 Hz), 8.11 (1H, d, J=7.9 Hz), 8.07 (1H, d, J=8.7 Hz), 8.02-7.97 (1H, m), 7.94-7.86 (2H, m), 7.84 (1H, d, J=7.7 Hz), 7.78-7.67 (2H, m), 7.61-7.53 (1H, m), 7.41-7.32 (2H, m), 6.88 (1H, s), 6.84 (1H, d, J=5.2 Hz), 6.52 (1H, s), 6.12 (1H, d, J=5.2 Hz); m/z (ES+) 459 [MH+].

Workup

  1. customPurification by flash column chromatography
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a99bb54dad624ad0830fad31a9437d05
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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