Methyl iodide → tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 930608

Reaktionsgleichung

Reaktionsgleichung von HRID 930608
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1.[CH3:24]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][C:9]=3[N:10]([CH3:24])[C:11]=2[CH:12]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57950374tert-butyl 7-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Produkt 1

HCID 57950375tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% weight dispersion in mineral oil, 4.19 g, 0.105 mol) was added portionwise to a solution of tert-butyl 7-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (23.6 g, 0.07 mol) in DMF (300 mL) at room temperature under N2. After 1 h, methyl iodide (14.8 g, 6.47 mL, 0.105 mol) was added, and the reaction was allowed to proceed for an additional 2 h. The mixture was quenched with H2O, upon which a solid precipitated out of solution. The suspension was therefore diluted to 2 L with H2O and filtered. The solids were washed thoroughly with water, then dissolved in CH2Cl2, dried over Na2SO4, filtered and concentrated to dryness. This provided the title compound (22.4 g, 91%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.41 (s, 1H), 7.30 (d, J=8.3 Hz, 1H), 7.17 (d, J=8.4 Hz, 1H), 4.60 (s, 2H), 3.81 (br t, 2H), 3.58 (s, 3H), 2.77 (t, J=5.4 Hz, 2H), 1.50 (s, 9H).

Aufarbeitung

  1. waitto proceed for an additional 2 h
  2. customThe mixture was quenched with H2O, upon which a solid
  3. customprecipitated out of solution
  4. additionThe suspension was therefore diluted to 2 L with H2O
  5. filtrationfiltered
  6. washThe solids were washed thoroughly with water
  7. dissolutiondissolved in CH2Cl2
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c6126ea26f40492283dfcc0fe546779e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296743B2

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