Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate → 1-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}pyridin-3-yl)cyclobutanol

HRID 735369Notes

Reaction equation

HRID 735369 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+].Br[C:23]1[C:28]([C:29]2([OH:33])[CH2:32][CH2:31][CH2:30]2)=[CH:27][CH:26]=[CH:25][N:24]=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[C:28]([C:29]4([OH:33])[CH2:32][CH2:31][CH2:30]4)=[CH:27][CH:26]=[CH:25][N:24]=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 772302671-(2-Bromopyridin-3-yl)cyclobutanol

Product 1

HCID 689000641-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}pyridin-3-yl)cyclobutanolYield 46.1%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (340 mg, 1.1 mmol) and 1-(2-bromopyridin-3-yl)cyclobutanol (228 mg, 1.0 mmol) according to the method of Example 6 Step 4. Purification by flash column chromatography eluting with a 0-10% diethyl ether/dichloromethane gradient gave 1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}pyridin-3-yl)cyclobutanol (200 mg, 46%). 1H NMR (500 MHz, CDCl3) δ 8.61 (1H, s), 8.29 (1H, d, J=2.2 Hz), 8.10-8.04 (2H, m), 8.01 (1H, d, J=8.7 Hz), 7.95 (1H, dd, J=1.6, 8.6 Hz), 7.88-7.81 (2H, m), 7.73-7.64 (2H, m), 7.40 (1H, dd, J=4.5, 7.8 Hz), 7.23-7.15 (2H, m), 5.01 (1H, s), 2.78-2.68 (4H, m), 2.42-2.34 (1H, m), 1.86-1.78 (1H, m); m/z (ES+) 434 [MH+].

Workup

  1. customPurification by flash column chromatography
  2. washeluting with a 0-10% diethyl ether/dichloromethane gradient

Sources & evidence

ORD record
ord-9bd59cca21b8450ebb0752c62b980a25
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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