Sodium Carbonate → N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-phenylthiophene-2-sulfonamide

HRID 234317Notes

Reaction equation

HRID 234317 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21][N:22]([C:32]1[O:36][N:35]=[C:34]([CH3:37])[C:33]=1[CH3:38])[S:23]([C:26]1[S:27][C:28](Br)=[CH:29][CH:30]=1)(=[O:25])=[O:24]>C(O)C.C1C=CC=CC=1.O.[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>[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21][N:22]([C:32]1[O:36][N:35]=[C:34]([CH3:37])[C:33]=1[CH3:38])[S:23]([C:26]1[S:27][C:28]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:29][CH:30]=1)(=[O:25])=[O:24]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 23359448N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

Product 1

HCID 53733365N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-phenylthiophene-2-sulfonamideYield 62%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium carbonate (2 ml of a 2M aqueous solution) followed by phenyl boronic acid (86 mg, 0.71 mmol) in 2 ml of 95% ethanol were added to a solution of N-(methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (200 mg, 0.47 mmol) and tetrakis (triphenylphosphine) palladium (0) (23 mg, 0.02 mmol) in dry benzene (4 ml) under argon. The mixture was refluxed for 12 h, diluted with 5 ml of water and extracted into ethyl acetate (3×25 ml). The combined organic extracts was washed with brine (1×25 ml), dried and evaporated. The residue was flash chromatographed on silica gel using 25% ethylacetate/hexanes to afford 123 mg (62%) of the sulfonamide as a colorless gum.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. extractionextracted into ethyl acetate (3×25 ml)
  3. washThe combined organic extracts was washed with brine (1×25 ml)
  4. customdried
  5. customevaporated
  6. customchromatographed on silica gel using 25% ethylacetate/hexanes

Sources & evidence

ORD record
ord-f41d3b33310a4abcb7a21ffd43fded96
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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