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

HRID 365467ノート

反応式

HRID 365467 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-97e920e5ef3f44a5afc1d1811b1613ca
出典データセット
uspto-grants-2000_10
特許番号
US06127390

反応ノート

読み込み中…