Pyridine → Methyl 5-(6-bromopyrazolo[1,5-a]pyridine-3-carboxamido)-6-methylnicotinate

HRID 335302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335302
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([OH:13])=O)[CH:7]=1.S(Cl)(Cl)=O.N1C=CC=CC=1.[NH2:24][C:25]1[C:26]([CH3:35])=[N:27][CH:28]=[C:29]([CH:34]=1)[C:30]([O:32][CH3:33])=[O:31]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([NH:24][C:25]2[C:26]([CH3:35])=[N:27][CH:28]=[C:29]([CH:34]=2)[C:30]([O:32][CH3:33])=[O:31])=[O:13])[CH:7]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 573723196-Bromopyrazolo(1,5-a)pyridine-3-carboxylic acidHCID 58662456Methyl 5-amino-6-methylnicotinate

Produkt 1

HCID 71282967Methyl 5-(6-bromopyrazolo[1,5-a]pyridine-3-carboxamido)-6-methylnicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

6-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (7.71 g, 32.0 mmol) in toluene (80 ml) was treated with thionyl chloride (18.67 ml, 256 mmol) and was heated to 110° C. for 6 hr. The solvent was removed in vacuo and the residue was treated with pyridine (80 ml), methyl 5-amino-6-methylnicotinate (4.25 g, 25.6 mmol) and oven dried molecular sieves. The reaction mixture was stirred at RT overnight and then treated with MeOH (250 ml). The resulting suspension was removed by filtration. The filtrate was triturated with methanol and the solid produced was isolated to afford the title compound;

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customdried molecular sieves
  3. additiontreated with MeOH (250 ml)
  4. customThe resulting suspension was removed by filtration
  5. customThe filtrate was triturated with methanol
  6. customthe solid produced
  7. customwas isolated

Quellen und Nachweise

ORD-Eintrag
ord-81bc49a1d6f942adb8158b8f2d564527
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883819B2

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