Benzenesulfonyl chloride → 1-Benzenesulfonyl-5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

HRID 60221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60221
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([F:14])[CH:12]=2)[NH:7][C:6]=1[CH3:15])=[O:4].[OH-].[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[C:6]=1[CH3:15])=[O:4]

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 58365050Methyl 5-fluoro-2-methyl-1H-pyrrolo[2,3-B]pyridine-3-carboxylate

Produkt 1

HCID 583651851-Benzenesulfonyl-5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A cooled (0-5° C.) suspension of 5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (9.0 g, 43.2 mmol), powdered sodium hydroxide (5.4 g, 133.9 mmol) and benzyltriethylammonium chloride (0.2 g, 0.86 mmol) in dichloromethane (100 mL) was treated over ca. 5 minutes with benzenesulfonyl chloride (9.5 g, 6.9 mL, 54.0 mmol). The reaction mixture was allowed to stir at 0-5° C. for 20 minutes then allowed to warm to ambient temperature and stirred for 24 hours. The solid was removed by filtration through celite and the cake washed with dichloromethane. The filtrate was evaporated and the resultant residue triturated with diethyl ether to afford the title compound as a cream solid (14.0 g, 93%). 1H NMR (400 MHz, CDCl3): 8.27 (dd, J=2.8, 1.1 Hz, 1H), 8.18-8.18 (m, 2H), 7.97 (dd, J=8.7, 2.8 Hz, 1H), 7.61-7.61 (m, 1H), 7.52-7.51 (m, 2H), 3.94 (s, 3H), 3.16 (s, 3H).

Aufarbeitung

  1. temperatureA cooled
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 24 hours
  4. customThe solid was removed by filtration through celite
  5. washthe cake washed with dichloromethane
  6. customThe filtrate was evaporated
  7. customthe resultant residue triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-283fc5e95c444d55995fdda501c270ac
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440976B2

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