Sodium hydride → tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

HRID 2423213

Reaktionsgleichung

Reaktionsgleichung von HRID 2423213
[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:12][CH:11]=[CH:10]3.[H-].[Na+].[CH3:25][C:26]1[O:30][N:29]=[CH:28][C:27]=1[S:31](Cl)(=[O:33])=[O:32]>CN(C=O)C>[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[N:12]([S:31]([C:27]1[CH:28]=[N:29][O:30][C:26]=1[CH3:25])(=[O:33])=[O:32])[CH:11]=[CH:10]3

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27761415-Methyl-1,2-oxazole-4-sulfonyl chlorideHCID 67242740tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate2×

Produkt 1

HCID 67242535tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylateAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 42, 25 mg, 0.083 mmol) was dissolved in DMF (1 mL) and sodium hydride (60% in mineral oil, 4.0 mg, 0.17 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes before 5-methyl-4-isoxazolesulfonyl chloride (21 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at room temperature overnight. The reaction was quenched by addition of water and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (0.010 g) which was dissolved in DCM (1 mL) and TFA (1 mL) was added. The reaction mixture was stirred at room temperature for 1 hour and the solvent was removed under reduced pressure. The crude material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (1 mg). MS m/z 348 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched by addition of water
  3. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-ea9a98092d084cb49091653962e54b87
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960374B2

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