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

HRID 1653899Notes

Reaction equation

HRID 1653899 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 (0.5 g) was added to a solution of isobutyl 5-ethenyl-2-hydroxybenzoate (6.6 g, 30 mmol) 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 7.2g (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-79cb0f483c004ab8a7445ed74f1fc7af
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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