Chlorosuccinimide → 6-Bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

HRID 1253456노트

반응식

HRID 1253456 반응식
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[Cl:13])[CH:7]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 446228256-Bromo-4-methoxypyrazolo[1,5-a]pyridine

생성물 1

HCID 672072806-Bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 6-bromo-4-methoxypyrazolo[1,5-a]pyridine (1010 mg, 4.43 mmol) in acetonitrile (40 ml) was added N-chlorosuccinimide (1180 mg, 8.86 mmol). The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and 1N aqueous sodium hydroxide (100 ml). The organic layer was washed with brine (100 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to afford 6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H); 8.03 (s, 1H); 6.84 (s, 1H); 3.94 (s, 1H). LRMS (ESI) calculated for C8H6BrClN2O [M+H]+, 260.9; found 261.0.

후처리

  1. customThe reaction mixture was partitioned between dichloromethane (100 ml) and 1N aqueous sodium hydroxide (100 ml)
  2. washThe organic layer was washed with brine (100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-919f76a87d674e6b952a82971b1d3693
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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