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

HRID 365467Notes

Reaction equation

HRID 365467 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-97e920e5ef3f44a5afc1d1811b1613ca
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

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