Triethylamine → N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

HRID 40652

Reaktionsgleichung

Reaktionsgleichung von HRID 40652
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:16]2[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=[C:12]([Br:11])[CH:17]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 596134182-Bromo-4-chloro-5-nitropyridine

Produkt 1

HCID 56926468N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amineAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of 2-bromo-4-chloro-5-nitropyridine (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6-DMSO, 400 MHz) δ 9.00 (br t, 1H, J=6.3 Hz), 8.80 (s, 1H), 7.35 (d, 2H, J=8.7 Hz), 7.10 (s, 1H), 6.95 (d, 2H, J=8.8 Hz), 4.60 (d, 2H, J=6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt=2.13 min; m/z (ESI−) 336, 338 (M−H).

Aufarbeitung

  1. washwas then washed successively with water and brine
  2. concentrationbefore being concentrated in vacuo to a light brown oil which

Quellen und Nachweise

ORD-Eintrag
ord-2e3d4c2515ea484f98336fd06b5114a8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530468B2

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