Toluene → N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(6-methoxy-2-pyridinyl)[1,1'-biphenyl]-2-sulfonamide

HRID 962608Notes

Reaction equation

HRID 962608 reaction equation
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[O:24][N:23]=[C:22]([CH3:25])[C:21]=1[CH3:26])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:12])=[O:11])(O)O.[C:27](=[O:30])([O-])[O-].[Na+].[Na+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][C:22]1[C:21]([CH3:26])=[C:20]([N:13]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[S:10]([C:5]2[C:4]([C:36]3[CH:37]=[CH:38][C:33]([C:39]4[CH:25]=[CH:22][CH:21]=[C:20]([O:30][CH3:27])[N:13]=4)=[CH:34][CH:35]=3)=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:12])=[O:11])[O:24][N:23]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide

Product 1

HCID 18660528N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(6-methoxy-2-pyridinyl)[1,1'-biphenyl]-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To 230 mg (0.87 mmol) of compound B, and 280 mg (0.73 mmol) of 2-Borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide in a mixture of 5.5 mL of degassed toluene and 3.7 mL of degassed ethanol, was added 84 mg (0.072 mmol) of tetrakis(triphenylphosphine) palladium(0) and 3.2 mL of degassed 2N aqueous sodium carbonate. The mixture was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and then brine, dried (magnesium sulfate) and evaporated. Flash chromatography (50 mm×6"; 30% to 40% to 50% ethyl acetate/hexane) afforded 172 mg of an oily-solid residue (45%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialbrine, dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-61e67e67672f40a1a0fdadddc7ea5ba3
Source dataset
uspto-grants-1998_06
Patent number
US05760038

Reaction notes

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