Triethylamine → 5-(Benzyloxy)-3-bromopicolinonitrile

HRID 340222

반응식

HRID 340222 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:21]#[N:22])(C)C.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]([C:21]#[N:22])=[N:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

생성물 1

HCID 671177075-(Benzyloxy)-3-bromopicolinonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

To a solution of 53-(benzyloxy)-5-bromopyridine 1-oxide (from step 2) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in hexane to give a mixture of two benzoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated en vacuo
  3. customthe residue was purified by a COMBIFLASH® system (ISCO)
  4. customto give
  5. additiona mixture of two benzoxy regioisomers, one of which

출처 및 근거

ORD 기록
ord-79c3e6c71bb74976b38875d78721c99b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895577B2

연결된 노트

불러오는 중…