Methylamine → 1-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide

HRID 1475323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475323
[CH3:1][NH2:2].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:19])=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:13]=2)[C:8]([CH3:21])([CH3:20])[CH2:7]1)(=[O:5])[CH3:4]>C1COCC1>[CH3:1][NH:2][S:15]([C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:21])([CH3:20])[CH2:7][N:6]2[C:3](=[O:5])[CH3:4])=[CH:10][C:11]=1[Br:19])(=[O:17])=[O:16]

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 867239431-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride

Produkt 1

HCID 709804931-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamideAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methylamine (2 M solution in THF, 2.4 mL, 4.9 mmol) was added to a solution of 1-acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride (300 mg, 0.82 mmol) in THF (10 mL). The solution was stirred at room temperature for 30 minutes then the solvent was removed in vacuo and the residue partitioned between water and EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (271 mg) as a yellow solid. 1H NMR (CDCl3): 8.93 (1H, s), 7.44 (1H, s), 5.07 (1H, s), 3.88 (2H, s), 2.68 (3H, d), 2.25 (3H, s), 1.48-1.22 (6H, s).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0c2394c4753c41aba27788f136bc4d90
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018214B2

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