Tributylamine → Isobutyl 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

HRID 742999Notes

Reaction equation

HRID 742999 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:16])=[C:7]([CH:15]=1)[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])=[CH2:2].I[C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CCCC)CCCC)CCC>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:16][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH:2][C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[O:9]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 1143526[(4-Iodophenyl)sulfonyl]-2-pyridylamineHCID 19423382Isobutyl 5-ethenyl-2-hydroxybenzoate

Product 1

HCID 53946052Isobutyl 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Palladium (II) acetate (0.15 g, 0.67 mmol) was added to a stirred solution of isobutyl 5-ethenyl-2-hydroxybenzoate (6.6 g, 30 mmol) and 4-iodo-N-2-pyridinylbenzenesulfonamide (10.8 g, 30 mmol) in dimethylacetamide (40 ml) and tributylamine (10 ml, 42 mmol) at 95° C. After 100 min. the solution was filtered and evaporated at 50°-60° C. (bath temp.) until solid material appeared. The mixture was diluted with isopropanol (0.5 1) and chilled in a freezer. The product was filtered off to yield 7.1g (52%).

Workup

  1. filtrationAfter 100 min. the solution was filtered
  2. customevaporated at 50°-60° C. (bath temp.) until solid material
  3. additionThe mixture was diluted with isopropanol (0.5 1)
  4. temperaturechilled in a freezer
  5. filtrationThe product was filtered off
  6. customto yield 7.1g (52%)

Sources & evidence

ORD record
ord-12a5b4f4d5974a719c0accbad3a937ae
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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