Sodium Carbonate → N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide

HRID 361452

Reaction equation

HRID 361452 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(B(O)O)[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.Cl[C:27]1[C:32]([S:33]([N:36]([C:46]([O:48][CH2:49][CH:50]([CH3:52])[CH3:51])=[O:47])[C:37]2[C:42]([O:43][CH3:44])=[N:41][C:40]([CH3:45])=[CH:39][N:38]=2)(=[O:35])=[O:34])=[CH:31][CH:30]=[CH:29][N:28]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[CH2:49]([O:48][C:46]([N:36]([C:37]1[C:42]([O:43][CH3:44])=[N:41][C:40]([CH3:45])=[CH:39][N:38]=1)[S:33]([C:32]1[C:27]([C:7]2[CH:12]=[CH:11][C:10]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:9][CH:8]=2)=[N:28][CH:29]=[CH:30][CH:31]=1)(=[O:35])=[O:34])=[O:47])[CH:50]([CH3:52])[CH3:51]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 2304781,4-Benzenediboronic acidHCID 11015197Isobutyl (2-chloropyridin-3-yl)sulfonyl(3-methoxy-5-methylpyrazin-2-yl)carbamate

Product 1

HCID 21186320N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamideYield 17.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0) (60 mg) was added to a deoxygenated solution of sodium carbonate (233 mg), 1,4-benzenediboronic acid (165 mg), 2-chloropyrimidine (114.5 mg) and 2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (414 mg) in a mixture of water (1.6 ml), ethanol (4 ml) and toluene (8 ml). The mixture was stirred and heated under argon under reflux for 16 hours and then allowed to cool to ambient temperature. Water (15 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with saturated sodium chloride solution and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 25-100% ethyl acetate/hexane to give N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide (95 mg) as a solid, mass spectrum (+ve ESP): 535 (M+H)+.

Workup

  1. temperatureheated under argon
  2. temperatureunder reflux for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  8. washeluting with 25-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d6cdd9d19ecf41cfba9abaad4019268c
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Linked notes

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