Water → HCID 178499173, 화합물

HRID 82063노트

반응식

HRID 82063 반응식
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.C([O-])(=O)C.[Na+].[Br:19]Br.O>C(O)(=O)C>[Br:19][C:8]1[CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2][NH:1][C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 178499174HCID 178499174, 화합물

생성물 1

HCID 178499173HCID 178499173, 화합물수율 31%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

A mixture of methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VI) (0.177 g, 1 mmol), sodium acetate (0.492 g, 6 mmol) and bromine (0.308 mL, 6 mmol) in glacial acetic acid (5 mL) was heated overnight at 120° C. in a sealed tube. The solution was cooled and poured into water. The solids formed were filtered, washed with water and dried at room temperature under vacuum. The crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH) to produce methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VII) as a white solid (78 mg, 0.31 mmol, 30% yield). 1H NMR (CDCl3) δ ppm 3.95 (s, 3 H), 8.62 (d, J=3.01 Hz, 1 H), 8.73 (d, J=3.01 Hz, 1 H); ESIMS Found for C8H6BrN3O2 m/z 256.3 (M+H).

후처리

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried at room temperature under vacuum
  6. customThe crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH)

출처 및 근거

ORD 기록
ord-003a1217fafc40f198bed5b0af3cfd44
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846714B2

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