N-Iodosuccinimide → 2-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1107487Notes

Reaction equation

HRID 1107487 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:13][C:14]([N:16]([C:36]1[C:41]([O:42][CH3:43])=[N:40][C:39]([CH3:44])=[CH:38][N:37]=1)[S:17]([C:20]1[C:21]([C:26]2[CH:31]=[CH:30][C:29]([Si](C)(C)C)=[CH:28][CH:27]=2)=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18])=[O:15])[CH:10]([CH3:12])[CH3:11]>C(#N)C>[I:1][C:29]1[CH:30]=[CH:31][C:26]([C:21]2[C:20]([S:17]([N:16]([C:14]([O:13][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:15])[C:36]3[C:41]([O:42][CH3:43])=[N:40][C:39]([CH3:44])=[CH:38][N:37]=3)(=[O:19])=[O:18])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide3×HCID 21186299N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-trimethylsilylphenyl)pyridine-3-sulphonamide

Product 1

HCID 211862652-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

N-Iodosuccinimide (0.84 g) was added to a solution of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-trimethylsilylphenyl)pyridine-3-sulphonamide (1.58 g) in acetonitrile (15 ml) and the reaction mixture was stirred and heated at 65° C. for 17 hours. A further portion of N-iodosuccinimide (50 mg) was added and heating continued for 24 hours, then more N-iodosuccinimide (100 mg) was added and heating continued a further 24 hours. The mixture was cooled and volatile material was removed by evaporation. The residue was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 0-25% ethyl acetate/hexane, followed by trituration with hexane (2×25 ml) to give 2-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide as a solid, m.p. 156-158° C.; 1H NMR (CDCl3): 0.7 (d, 6H), 1.7 (m, 1H), 2.5 (s, 3H), 3.8 (d, 2H), 4.0 (s, 3H), 7.4 (d, 2H), 7.5 (dd, 1H), 7.7 (d, 2H), 7.9 (s, 1H), 8.8 (dd, 1H), 8.9 (dd, 1H); mass spectrum (+ve ESP): 583 (M+H)+.

Workup

  1. temperatureheating
  2. temperatureheating
  3. waitcontinued a further 24 hours
  4. temperatureThe mixture was cooled
  5. customvolatile material was removed by evaporation
  6. customThe residue was purified by chromatography on a silica gel Mega Bond Elut column
  7. washeluting with 0-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-778c31ef4f7742ba8ee5456213ca9236
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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