4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide → Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

HRID 1653900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1653900
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:14])=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[CH:2].I[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1>O1CCCC1.C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[OH:14][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

7

Edukt 2

HCID 37926154-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamideHCID 19423366Ethyl 5-ethynyl-2-hydroxybenzoate

Produkt 1

HCID 19423387Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0.29 g, 0.25 mmol) and copper(I)iodide (0.095 g, 0.5 mmol) were added to a solution of ethyl 5-ethynyl-2-hydroxybenzoate (10.5g, 55 mmol) and 4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide (18.7 g, 50 mmol) in tetrahydrofuran (75 ml) and triethylamine (75 ml) at 55° C. After 2 h the solid product was collected with filtration and washed with hydrochloric acid (1M). The material was boiled in formic acid (300 ml ) for 15 min. and filtered. Water (200 ml) was added and the product crystallized upon cooling. Yield 17.3 g (79%). 1H-NMR (Pyridine-d5 as solvent)

Aufarbeitung

  1. filtrationAfter 2 h the solid product was collected with filtration
  2. washwashed with hydrochloric acid (1M)
  3. filtrationfiltered
  4. additionWater (200 ml) was added
  5. customthe product crystallized
  6. temperatureupon cooling

Quellen und Nachweise

ORD-Eintrag
ord-48bbb154fa4f4a059c3e0969fb7820d4
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05403930

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