m-Chloroperbenzoic acid → Methyl 2-{[2-(4-fluorophenyl)-1-oxidoquinolin-6-yl]sulfonyl}benzoate

HRID 735334Notes

Reaction equation

HRID 735334 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([S:29]([C:32]4[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=4[C:34]([O:36][CH3:37])=[O:35])(=[O:31])=[O:30])[CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1.[OH-].[Ca+2].[OH-]>ClCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([S:29]([C:32]4[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=4[C:34]([O:36][CH3:37])=[O:35])(=[O:31])=[O:30])[CH:25]=3)[N+:20]=2[O-:6])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 68900676Methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]sulfonyl}benzoate

Product 1

HCID 68901634Methyl 2-{[2-(4-fluorophenyl)-1-oxidoquinolin-6-yl]sulfonyl}benzoateYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (77%; 82 mg, 0.37 mmol) was added to a solution of methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]sulfonyl}benzoate [Example 30] (103 mg, 0.24 mmol) in dichloromethane (10 mL). The resulting mixture was stirred at room temperature under nitrogen for 2 days. Calcium hydroxide (308 mg, 4.16 mmol) was added and the resulting slurry stirred for 2 hours. The mixture was filtered and the filter cake washed thoroughly with dichloromethane. The filtrate was evaporated and the residue purified by flash chromatography, eluting with 10-25% diethyl ether/dichloromethane, followed by trituration with diethyl ether to give the title compound as a pale yellow solid (45 mg, 42%). 1H NMR (500 MHz, CDCl3) δ 8.94 (1H, d, J 9.2 Hz), 8.60 (1H, s), 8.28 (1H, m), 8.19 (1H, dd, J 1.6, 9.2 Hz), 8.02 (2H, dd, J 5.4, 8.7 Hz), 7.87 (1H, d, J 8.7 Hz), 7.71-7.61 (4H, m), 7.22 (2H, t, J 8.6 Hz), 3.95 (3H, s); m/z (ES+) 438 [MH+].

Workup

  1. stirringthe resulting slurry stirred for 2 hours
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed thoroughly with dichloromethane
  4. customThe filtrate was evaporated
  5. customthe residue purified by flash chromatography
  6. washeluting with 10-25% diethyl ether/dichloromethane

Sources & evidence

ORD record
ord-4f8ae0f374f4407a93444178013d1f27
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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