Hydrochloric Acid → 3-(6-Bromo-4-methyl-1H-benzimidazol-2-yl)-4-chloro-1H-pyridin-2-one

HRID 1354610Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[N:9]=[C:8]([C:10]3[C:11]([O:17]C)=[N:12][CH:13]=[CH:14][C:15]=3I)[NH:7][C:6]=2[CH:19]=1.[ClH:21]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[N:9]=[C:8]([C:10]3[C:11](=[O:17])[NH:12][CH:13]=[CH:14][C:15]=3[Cl:21])[NH:7][C:6]=2[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The suspension of 6-bromo-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole (4 g, 9.03 mmol) and 60 mL of 4 M HCl in dioxane was heated to 80° C. for 6 h and cooled to room temperature. The precipitate was filtered and dried to yield the title compound (3.0 g, 100%) as a brown powder. The crude product was used for the next step without purification. 1H NMR (300 MHz, CD3OD) δ 7.55 (1H, s), 7.42 (1H, d, J=6.0 Hz), 7.17 (1H, s), 6.91 (1H, d, J=6.0 Hz), 2.55 (3H, s). LC MS (M+H)+ m/z 338 (t=1.33 min.).

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtered
customdried

Sources & evidence

ORD record: ord-3f8329231d804a819f924b46b0f10089
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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