Tributylamine → Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

HRID 1464162Notes

Reaction equation

HRID 1464162 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[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CCCC)CCCC)CCC>[Pd].CC(N(C)C)=O>[OH:16][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH:2][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]3[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:20][CH:19]=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 3792615HCID 3792615, compoundHCID 19423382Isobutyl 5-ethenyl-2-hydroxybenzoate

Product 1

HCID 54356729Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoateYield 51.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

10% Palladium on charcoal (0.5g) was added to a solution of isobutyl 5-ethenyl-2-hydroxybenzoate (6.6 g, 30mmol) and 4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide (11.2 g, 30 mmol) in dimethylacetamide (10 ml) and tributylamine (10 ml, 42 mmol) at 110° C. After 90 min. the solution was filtered and diluted with isopropanol (0.3 l) and chilled in a freezer. The product was filtered off, dried and dissolved in boiling formic acid (100 ml). The solution was filtered and water (65 ml) was added. After cooling to refrigerator temperature the product was filtered off and dried to yield 7.2 g (51%) product

Workup

  1. filtrationAfter 90 min. the solution was filtered
  2. additiondiluted with isopropanol (0.3 l)
  3. temperaturechilled in a freezer
  4. filtrationThe product was filtered off
  5. customdried
  6. dissolutiondissolved
  7. filtrationThe solution was filtered
  8. additionwater (65 ml) was added
  9. temperatureAfter cooling to refrigerator temperature the product
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-87e8454b11784379b44bdfe542a751f5
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

Loading…