Acetic Anhydride → 1-(4-methoxybenzyl)-6-bromo-1H-imidazo[4,5-c]pyridine

HRID 40669

Reaction equation

[C:1](OC(=O)C)(=O)C.[CH3:8][O:9][C:10]1[CH:25]=[CH:24][C:13]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([Br:22])[N:19]=[CH:18][C:17]=2[NH2:23])=[CH:12][CH:11]=1>C(OC(OCC)OCC)C>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:16]3[CH:21]=[C:20]([Br:22])[N:19]=[CH:18][C:17]=3[N:23]=[CH:1]2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Acetic anhydride (1.28 mL, 13.6 mmol) was added to a solution of N4-(4-methoxybenzyl)-6-bromopyridine-3,4-diamine (1.05 g, 3.41 mmol) in triethylorthoformate (13 mL). The mixture was heated at 100° C. for 18 hours and then concentrated to give the title compound as a brown oil (1.18 g, quantitative). 1H NMR (d6-DMSO, 400 MHz) δ 8.75 (s, 1H), 8.60 (s, 1H), 8.00 (s, 1H), 7.35 (d, 2H, J=8.8 Hz), 6.90 (d, 2H, J=8.8 Hz), 5.45 (s, 2H), 3.70 (s, 3H). LCMS (2) Rt=2.27 min; m/z (ESI+) 318, 320 (MH+).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-fcb72d219da742d98707cf3c655e880c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530468B2

Linked notes

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