Pyridine → methyl 2-(4-(4-(2,4-dichlorophenylsulfonamido)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)-3-methoxyphenyl)acetate

HRID 2423312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423312
[NH2:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=2[O:23][CH3:24])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30].[Cl:33][C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:35]=1[S:41](Cl)(=[O:43])=[O:42].N1C=CC=CC=1>ClCCl>[Cl:33][C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:35]=1[S:41]([NH:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=2[O:23][CH3:24])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])(=[O:43])=[O:42]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 59864774Methyl 2-(4-(4-amino-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)-3-methoxyphenyl)acetate

Produkt 1

HCID 59864905methyl 2-(4-(4-(2,4-dichlorophenylsulfonamido)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)-3-methoxyphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 2-(4-(4-amino-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)-3-methoxyphenyl)acetate (42 mg, 0.092 mmol) in dichloromethane (1 mL) was added 2,4-dichlorobenzene sulfonyl chloride (25 mg, 0.1 mmol) and pyridine (10 μl, 0.12 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was then diluted with dichloromethane (20 mL) and washed with dilute aqueous hydrochloric acid (20 mL) and water (20 mL), then dried over magnesium sulfate and concentrated under reduced pressure. The desired sulfonamide was isolated by column chromatography (10% ethyl acetate/hexane). 1H NMR (400 MHz) (CDCl3) δ 8.40 (s, 1H); 7.81 (s, 1H); 7.72 (d, J=8.5 Hz, 1H); 7.32 (d, J=9 Hz, 1H); 7.19 (d, J=1.9 Hz, 1H); 7.15 (dd, J=1.9, 8.5 Hz, 1H); 6.90 (d, J=1.8 Hz, 1H); 6.88 (d, J=9 Hz, 1H); 6.60 (dd, J=1.8, 8.2 Hz, 1H); 6.35 (d, J=8.2 Hz, 1H); 5.68 (s, 2H); 3.84 (s, 3H); 3.75 (s, 3H), 3.62 (s, 2H); 3.57 (t, J=8.2 Hz, 2H); 0.89 (t, J=8.2 Hz, 2H), 0.0 (s, 9H).

Aufarbeitung

  1. washwashed with dilute aqueous hydrochloric acid (20 mL) and water (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c154900681a4442940d0597137033bd
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960567B2

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