Dimethylformamide → 4-(4-Bromo-2-butyl-5-formyl-imidazol-1-ylmethyl)benzoic acid methyl ester

HRID 341381Notes

Reaction equation

[Br:1][C:2]1[N:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH3:10])[NH:4][C:3]=1[CH:11]=[O:12].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1>>[CH3:33][O:32][C:30](=[O:31])[C:29]1[CH:34]=[CH:35][C:26]([CH2:25][N:4]2[C:3]([CH:11]=[O:12])=[C:2]([Br:1])[N:6]=[C:5]2[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:27][CH:28]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 256687Methyl 4-(bromomethyl)benzoate

HCID 178441570HCID 178441570, compound

Product 1

HCID 574839434-(4-Bromo-2-butyl-5-formyl-imidazol-1-ylmethyl)benzoic acid methyl esterYield 38.9%

Procedure

5-Bromo-2-butyl-3H-imidazole-4-carbaldehyde (38 g, 160 mmol) was dissolved in DMF (400 mL, 5 mol). Potassium carbonate (27 g, 200 mmol) was added followed by methyl 4-bromomethylbenzoate (38 g, 160 mmol) and the solution was stirred at room temperature overnight. The mixture was then concentrated and purified by silica gel chromatography (0-50% EtOAc:hexanes) to yield intermediate (9a) (32.2 g, 62.2 mmol). MS m/z: [M+H+] calcd for C17H19N2O3Br, 379.3; found 379.1. 1H-NMR (400 Mz, CD3OD) δ (ppm): 0.82 (t, 3H, J=5 Hz), 1.28 (m, 2H), 1.54 (q, 2H, J=5 Hz), 2.70 (t, 2H, J=5 Hz), 5.69 (s, 2H), 7.15 (d, 2H, J=5 Hz), 7.96 (d, 2H, J=5 Hz), 9.66 (s, 1H).

Workup

concentrationThe mixture was then concentrated
custompurified by silica gel chromatography (0-50% EtOAc:hexanes)

Sources & evidence

ORD record: ord-41fbd32a228e4687bbff46e2cfa7cc33
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895755B2

Reaction notes

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