Methylamine → 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide

HRID 1037525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037525
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17](O)=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][NH2:27].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:27][CH3:26])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 24813Phosphorus oxychlorideHCID 677745202-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

Produkt 1

HCID 677763242-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of compound (vii) (2.2 g, 5.5 mmol) in pyridine (45 mL) was added methyl amine (8.2 mL, 2 M solution in THF, 16 mmol). The reaction mixture was cooled to 0° C. and POCl3 (2.88 g, 19 mmol) was added dropwise at the same temperature. After 1 h TLC and LCMS showed the absence of SM and formation of product. The reaction mixture was quenched in ice water and the precipitate was filtered and crystallized from MeOH to give 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide (viii) (1.25 g, 55%). ESI-MS m/z calculated for [M+H]+: 415.04/417.04; found: 415.15/417.15.

Aufarbeitung

  1. customThe reaction mixture was quenched in ice water
  2. filtrationthe precipitate was filtered
  3. customcrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-367c7fe9133542a596cac735c023d700
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546389B2

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