Cesium fluoride → 3-(6-Imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

HRID 1354636Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[C:8]([CH3:23])[C:9]3[N:13]=[C:12]([C:14]4[C:15](=[O:21])[NH:16][CH:17]=[CH:18][C:19]=4I)[NH:11][C:10]=3[CH:22]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:24][OH:25].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[F-].[Cs+]>CN(C=O)C>[N:1]1([C:6]2[CH:7]=[C:8]([CH3:23])[C:9]3[N:13]=[C:12]([C:14]4[C:15](=[O:21])[NH:16][CH:17]=[CH:18][C:19]=4[O:25][CH2:24][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=4)[NH:11][C:10]=3[CH:22]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one (25 mg, 0.06 mmol) in DMF (2 mL) were added pyridine carbinol (26 mg, 0.24 mmol) and cesium fluoride (36 mg, 0.24 mmol). The reaction mixture was heated to 130° C. for 14 h and cooled to room temperature. After concentration in vacuo, the residue was purified by prep. HPLC to yield the title compound (8.2 mg, 34%). 1H NMR (300 MHz, CD3OD) δ 9.58 (1H, narrow d, J=1.2 Hz), 8.92 (1H, d, J=4.9 Hz), 8.19 (1H, narrow t, J=1.2 Hz), 8.12 (1H, s), 7.97–8.02 (2H, m), 7.85 (1H, narrow t, J=1.8 Hz), 7.81 (1H, narrow t, J=1.0 Hz), 7.63 (1H, d, J=7.9 Hz), 7.54 (1H, t, J=6.2 Hz), 6.81 (1H, J=7.5 Hz), 5.86 (2H, s), 2.86 (3H, s). LCMS (M+H)+ m/z 399 (t=1.07 min.).

Workup

temperaturecooled to room temperature
concentrationAfter concentration in vacuo
customthe residue was purified by prep

Sources & evidence

ORD record: ord-1473a224819a4327a601156ffc4b3a3b
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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