M-Cresol → 5-(4'-Cyanobenzyl)-1-[2-(3"-methylphenylphenoxy)-pyrid-5-ylmethyl)imidazole

HRID 365469Notes

Reaction equation

[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17](Br)=[N:18][CH:19]=3)[CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH:23]1[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=1C.[H-].[Na+].N#N>CN(C=O)C>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:29][C:28]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:5]4[CH:6]=[CH:21][CH:22]=[C:3]([CH3:1])[CH:4]=4)=[N:18][CH:19]=3)[CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 110 °C

Procedure

The compound from Example 1 Step 3 (0.11 g 0.20 mmol), m-cresol (0.064 g, 0.59 mmol) and sodium hydride (60% dispersion in oil, 4.0 equiv, 0.032 g) were suspended in DMF (0.5 mL) in an N2 purged sealed tube and heated at 110° C. for 24 hr. The residue was dissolved in methanol and purified on a C18 preperative hplc column. Lyophilized from dioxane/HCl to provide the title compound. FAB-MS: calc: 380.4 found: 381.0. 2 1H-NMR (CD3OD): 2.4 ppm (s, 3H); 4.2 ppm (s, 2H); 5.4 ppm (s, 2H); 6.8-7.6 ppm (11H); 7.9 ppm (s, 1H); 9.1 ppm (s,1H).

Workup

custompurged
customsealed tube
dissolutionThe residue was dissolved in methanol
custompurified on a C18 preperative hplc column

Sources & evidence

ORD record: ord-366ab197e2c04d6eac991c86c1f0ace1
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127390

Reaction notes

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