Methylamine → 6-Bromo-N-methyl-2-oxoindoline-5-carboxamide

HRID 2245543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245543
CN.[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[O:13])[NH:10]2)=[CH:6][C:5]=1[C:14]([OH:16])=O.F[B-](F)(F)F.[N:22]1(OC(N(C)C)=[N+](C)C)[C:26]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[O:13])[NH:10]2)=[CH:6][C:5]=1[C:14]([NH:22][CH3:26])=[O:16]

Komponenten

8

Edukt 6

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 10192821HCID 10192821, Verbindung

Produkt 1

HCID 102362866-Bromo-N-methyl-2-oxoindoline-5-carboxamideAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methylamine (0.75 mL, 2.0 M in tetrahydrofuran) was added to a stirred solution of 6-bromo-2-oxoindoline-5-carboxylic acid (0.246 g, 0.96 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.369 g, 1.15 mmol), 1-hydroxybenzotriazole hydrate (0.176 g, 1.15 mmol), and diisopropylethylamine (0.55 mL, 3.16 mmol) in dry N,N-dimethylformamide (4 mL) under an atmosphere of nitrogen. The resulting mixture was stirred at room temperature for 1.5 h. An aqueous solution of sodium bicarbonate was added and the solvent was evaporated. The resulting residue was purified on a silica gel column using dichloromethane/methanol, (9:1), as the eluent to give 0.125 g (48% yield) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.27 (s, 1H), 7.11 (s, 1H), 3.20 (m, 2H), 3.09 (s, 3H); MS (ES) m/z 269 and 271 (M++1).

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe resulting residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-73520ba9d3f54d63800a625675644c8a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683067B2

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