Toluene → HCID 23226635, compound

HRID 361419Notes

Reaction equation

HRID 361419 reaction equation
Cl[C:2]1[C:7]([S:8]([N:11]([C:20]2[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=2)[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:29][S:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(O)C>[CH3:27][O:26][C:25]1[C:20]([N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[S:8]([C:7]2[C:2]([C:34]3[CH:35]=[CH:36][C:31]([S:30][CH3:29])=[CH:32][CH:33]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)(=[O:10])=[O:9])=[N:21][CH:22]=[C:23]([CH3:28])[N:24]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 21186249HCID 21186249, compound

Product 1

HCID 23226635HCID 23226635, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.022 g) was added to a deoxygenated mixture of 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl) ethoxymethyl]pyridine-3-sulphonamide (0.405 g), 4-methylthiophenylboronic acid (obtained by the procedure described in Tetrahedron Lett., 1993, 34, 8237) (0.148 g), toluene (4.5 ml), ethanol (2.5 ml) and 2M sodium carbonate solution (7 ml) and the mixture was stirred and heated under reflux for 18 hours. Water was added and the mixture was extracted three times with ethyl acetate. The organic extracts were combined, washed with saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-35% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-methylthiophenyl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.415 g) as an oil; 1H NMR (CDCl3): 0.0 (s, 9 H), 0.8 (t, 2 H), 2.5 (s, 3 H), 2.55 (s, 3 H), 3.6 (t, 2 H), 3.9 (s, 3 H), 4.8 (s, 2 H), 7.3-7.5 (m, 3 H), 7.6-7.7 (m, 2 H), 7.8 (s, 1 H), 8.7 (dd, 1 H), 8.8 (dd, 1 H); mass spectrum (+ve ESP): 533 (M+H)+.

Workup

  1. customobtained by the procedure
  2. temperatureheated
  3. temperatureunder reflux for 18 hours
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by gradient elution with 0-35% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-5f09676ba963415c9298a342d3741b99
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

Loading…