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

HRID 1521334노트

반응식

HRID 1521334 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-53cceb0558e34c3489ef2261b591c60d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073921B2

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