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

HRID 1521334Notes

Reaction equation

HRID 1521334 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

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;

Workup

  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

Sources & evidence

ORD record
ord-53cceb0558e34c3489ef2261b591c60d
Source dataset
uspto-grants-2015_07
Patent number
US09073921B2

Reaction notes

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