2-Bromopyridine → HCID 68898962, compound

HRID 735370Notes

Reaction equation

HRID 735370 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[CH:28]=[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[CH:28]=[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 79732-BromopyridineHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68898962HCID 68898962, compoundYield 34.8%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (250 mg, 0.81 mmol) and 2-bromopyridine (76 μL, 0.79 mmol) according to the method of Example 6 Step 4. Purification by flash column chromatography eluting with a 20-40% ethyl acetate/isohexane gradient gave 2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}pyridine (0.10 g, 34%). 1H NMR (400 MHz, CDCl3) δ 8.70 (1H, s), 8.68-8.65 (1H, m), 8.33-8.22 (1H, m), 8.07 (1H, d, J=8.6 Hz), 8.04-7.92 (4H, m), 7.82 (1H, dd, J=1.8, 8.6 Hz), 7.69-7.65 (2H, m), 7.46-7.44 (1H, m), 7.22-7.16 (2H, m); m/z (ES+) 364 [MH+].

Workup

  1. customPurification by flash column chromatography
  2. washeluting with a 20-40% ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-e7dab5a2f34948d3baae11484467dc4e
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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