Toluene → N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-2-[1-(phenylsulfonyl)-1H-indol-2-yl]benzenesulfonamide

HRID 1585673Notes

Reaction equation

HRID 1585673 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([O-])([O-])=O.[Na+].[Na+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CCO>[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[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:14]2[N:13]([S:10]([C:5]3[CH:4]=[CH:9][CH:8]=[CH:7][CH:6]=3)(=[O:11])=[O:12])[C:38]3[C:33]([CH:39]=2)=[CH:34][CH:35]=[CH:36][CH:37]=3)(=[O:12])=[O:11])[O:24][N:23]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide2×

Product 1

HCID 21219231N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-2-[1-(phenylsulfonyl)-1H-indol-2-yl]benzenesulfonamideYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (230 mg; 10 mol %) was added to a degassed solution of the title product of Step (A) (766 mg; 2 mmol) and the title product of Step (B) (900 mg; 2.34 mmol) in 10 ml of toluene and 8.5 ml of EtOH under argon. After adding 7 ml of 2M Na2CO3, the heterogeneous mixture was heated to 85° C. for 5 hrs with vigorous stirring. At this time, an additional amount of the title product of Step (B) (100 mg; 0.26 mmol) was added and the mixture was heated an additional 2 hrs. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (75 ml) and water (50 ml). The organic layer was washed with brine (50 ml), dried (MgSO4), and concentrated to afford a yellow residue which was chromatographed on a 5×20 cm silica gel column, using 4 L EtOAc:Hexanes, 3:7, 2 L EtOAc:hexanes, 4:6 and 1 L EtOAc:Hexanes, 1:1 as the mobile phase. The pure fractions were concentrated to afford 222 mg (19%) of the title product of this step as a light yellow foam.

Workup

  1. temperaturethe mixture was heated an additional 2 hrs
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate (75 ml) and water (50 ml)
  4. washThe organic layer was washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford a yellow residue which
  8. customwas chromatographed on a 5×20 cm silica gel column
  9. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-33ccfac8397243228ecae8a289d0a6f6
Source dataset
uspto-grants-1999_08
Patent number
US05939446

Reaction notes

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