2-Bromo-5-bromomethylpyridine → 5-(4-Cyanobenzyl)-1-(2-bromopyrid-5-ylmethyl)imidazole

HRID 365467노트

반응식

HRID 365467 반응식
C([N:20]1[CH:24]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41]Br)=[CH:37][N:36]=1>CN(C=O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][C:23]2[N:22]([CH2:41][C:38]3[CH:39]=[CH:40][C:35]([Br:34])=[N:36][CH:37]=3)[CH:21]=[N:20][CH:24]=2)=[CH:31][CH:30]=1)#[N:33]

참가 물질

4

반응물 2

HCID 64246602-Bromo-5-bromomethylpyridineHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

생성물 1

HCID 232920655-(4-Cyanobenzyl)-1-(2-bromopyrid-5-ylmethyl)imidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a flask was charged 1-trityl -4-p-cyanobenzyl imidazole (2.77 mmol, 1.18 g) from Step 1 and 2-bromo-5-bromomethyl pyridine (2.77 mmol, 0.67 g) from Step 2 in DMF (10 mL) and the mixture heated at 100° C. for 6 hr. The DMF was then removed in vacuo and the residue was triturated with ethyl ether. The ethyl ether was then decanted off and replaced with methanol (20 mL). This solution was then refluxed for 4 hr, cooled to ambient temperature and purified on a C18 preperative hplc column to provide the title compound. High resolution FAB-MS: calc; 353.040183 found; 353.040183. 1H-NMR (CD3OD): 4.2 ppm (s, 2H); 5.4 ppm (s, 2H); 7.2 and 7.6 ppm (d, 2H); 8.1 ppm (s, 1H); 9.1 ppm (s, 1H).

후처리

  1. customThe DMF was then removed in vacuo
  2. customthe residue was triturated with ethyl ether
  3. customThe ethyl ether was then decanted off
  4. temperatureThis solution was then refluxed for 4 hr
  5. temperaturecooled to ambient temperature
  6. custompurified on a C18 preperative hplc column

출처 및 근거

ORD 기록
ord-97e920e5ef3f44a5afc1d1811b1613ca
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127390

반응 노트

불러오는 중…