8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide → 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-vinylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

HRID 457335

Reaktionsgleichung

Reaktionsgleichung von HRID 457335
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:34]=[CH:33][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:30]([NH2:32])=[O:31])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]#[CH:29])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1>CN(C=O)C.CS(C)=O>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:34]=[CH:33][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:30]([NH2:32])=[O:31])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]=[CH2:29])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

3

Edukt 1

HCID 222915468-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Produkt 1

HCID 222916928-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-vinylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3013483N,N-dimethylformamide; methylsulfinylmethaneLösungsmittel

Versuchsvorschrift

A solution of 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (557 mg, 1.19 mmol) in DMF-DMSO (20 mL-1 mL) was treated at RT with H2 (5 psi) and Pd—CaSO4 (5%, 100 mg) for 12 min. The mixture was filtered through celite pad, concentrated and added water. The solid product was collected via filtration, washed with water and ether, and dried to give product (262 mg, 47%). 1H NMR was consistent with its structure.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite pad
  2. concentrationconcentrated
  3. additionadded water
  4. filtrationThe solid product was collected via filtration
  5. washwashed with water and ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a8d45760e38e424fbd2163fe3a51c169
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186743B2

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