Sodium Carbonate → N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamide

HRID 1956965Notes

Reaction equation

HRID 1956965 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])COCCOC)(=[O:12])=[O:11])(O)O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:34]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:38][C:35]=1[CH:36]=[O:37]>C1(C)C=CC=CC=1.CCO.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>[CH3:25][C:22]1[C:21]([CH3:26])=[C:20]([NH:13][S:10]([C:5]2[C:4]([C:34]3[CH:41]=[CH:40][C:39]([C:42]4[N:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:38][C:35]=3[CH:36]=[O:37])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:11])=[O:12])[O:24][N:23]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamideHCID 186631922-Bromo-5-(2-pyrimidinyl)benzaldehyde

Product 1

HCID 18663185N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamideYield 116.3%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 0.554 g (1.188 mmol) of 2-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide (prepared as described in U.S. patent application Ser. No. 08/603,975, filed Feb.20, 1996 by Murugesan et al. (Attorney Docket No. HA662d)) and 0.0578 g (0.05 mmol) of tetrakis(triphenylphosphine)-palladium(0) in 20 mL of toluene under argon, 10 mL of 2M aqueous sodium carbonate was added followed by 0.25 g (0.95 mmol) of the title compound of Step E added in 10 mL of 95% EtOH. The mixture was refluxed for 2 hrs and then diluted with 100 mL of water and extracted with 3×50 mL of EtOAc. The combined organic extracts were washed once with 100 mL of brine and dried and evaporated. The residue was chromatographed on 100 mL of silica gel using Hexanes/EtOAc 1:1 to afford 0.48 g (80%) of the title compound of this step as a colorless gum.

Workup

  1. temperatureThe mixture was refluxed for 2 hrs
  2. extractionextracted with 3×50 mL of EtOAc
  3. washThe combined organic extracts were washed once with 100 mL of brine
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on 100 mL of silica gel

Sources & evidence

ORD record
ord-0bd75b1ef4ed4203958c6bb7fe1546dc
Source dataset
uspto-grants-1998_07
Patent number
US05780473

Reaction notes

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