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

HRID 743002노트

반응식

HRID 743002 반응식
[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]

참가 물질

6

반응물 3

HCID 7622TributylamineHCID 37926154-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamideHCID 19423382Isobutyl 5-ethenyl-2-hydroxybenzoate

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 31374Dimethylacetamide용매

실험 절차

10% Palladium on charcoal (0.5g) was added to a solution of isobutyl 5-ethenyl-2-hydroxybenzoate (6.6g, 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 (0.31) 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

후처리

  1. filtrationAfter 90 min. the solution was filtered
  2. additiondiluted with isopropanol (0.31)
  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

출처 및 근거

ORD 기록
ord-9190a7f6bb9848d6ab8d65d4e00ec5ad
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556855

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