HCID 71295558, compound → HCID 178517591, compound

HRID 1776882Notes

Reaction equation

HRID 1776882 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:14][C:13]3[CH2:15][CH2:16][CH2:17][CH2:18][C:12]=3[N:11]=2)[C:5]([O:8]C)=[N:6][CH:7]=1>Br.CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][C:12]3[CH2:18][CH2:17][CH2:16][CH2:15][C:13]=3[N:14]=2)[C:5]([OH:8])=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 71295558HCID 71295558, compound

Product 1

HCID 178517591HCID 178517591, compoundYield 130.8%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 2-(5-bromo-2-methoxypyridin-3-yl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole (0.8 g, 2.6 mmol) in HBr/AcOH (10 mL), was heated to 100° C. for 12 hours. The solvent was removed off and the resulting residue was washed with dichloromethane (2*20 mL), then dry to provide 5-bromo-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)pyridin-2-ol (1 g, yield 100%) as a solid. 1HNMR (400 MHz, DMSO) δ 13.87 (br, 2H), 8.40 (d, J=2.7 Hz, 1H), 8.03 (d, J=2.7 Hz, 1H), 2.61 (s, 4H), 1.76 (s, 4H). MS (M+H)+: 294/296.

Workup

  1. customThe solvent was removed off
  2. washthe resulting residue was washed with dichloromethane (2*20 mL)
  3. customdry

Sources & evidence

ORD record
ord-b06735c909174e118baff9f477cb21d4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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