Ethanol → HCID 21186251, compound

HRID 361446Notes

Reaction equation

HRID 361446 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].COB(OC)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([S:31]([NH:34][C:35]3[C:40]([O:41][CH3:42])=[N:39][C:38]([CH3:43])=[CH:37][N:36]=3)(=[O:33])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:21][CH:20]=1.C(O)C>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>[CH3:42][O:41][C:40]1[C:35]([NH:34][S:31]([C:30]2[C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:10]4[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=4)=[CH:20][CH:21]=3)=[N:26][CH:27]=[CH:28][CH:29]=2)(=[O:33])=[O:32])=[N:36][CH:37]=[C:38]([CH3:43])[N:39]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2737238HCID 2737238, compoundHCID 21186371HCID 21186371, compound

Product 1

HCID 21186251HCID 21186251, compoundYield 36.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (25 mg) was added to a deoxygenated solution of sodium carbonate (223 mg), dimethoxy-(3-pyridyl)borane (116 mg) and 2-(4-iodophenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (828 mg) in a mixture of water (1.8 ml), ethanol (3 ml) and toluene (6 ml). The mixture was stirred and heated under argon at 85° C. for 17 hours and then allowed to cool to ambient temperature. Water was added and the reaction mixture was washed three times with ethyl acetate. The aqueous layer was acidified to pH 7 with 2M hydrochloric acid and extracted six times with ethyl acetate. These extracts were combined, washed with saturated sodium chloride solution then 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 0-8% methanol/dichloromethane to give N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[3-pyridyl]phenyl)pyridine-3-sulphonamide (123 mg) as a solid; 1H NMR (CDCl3): 2.3 (s, 3 H), 3.7 (s, 3 H), 7.3-7.7 (m, 7 H), 7.92 (m, 1 H), 8.55-8.75 (m, 2 H), 8.8 (dd, 1 H), 8.9 (d, 1 H); mass spectrum (+ve ESP): 434 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. washthe reaction mixture was washed three times with ethyl acetate
  3. extractionextracted six times with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialthen dried (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 0-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-830cea4a195e41c5ad2e971c1fb3bbe4
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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