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

HRID 1521334ノート

反応式

HRID 1521334 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-53cceb0558e34c3489ef2261b591c60d
出典データセット
uspto-grants-2015_07
特許番号
US09073921B2

反応ノート

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