Acetanilide → 2-Methyl-3-phenyl-3H-imidazo[4,5-b]pyridine

HRID 1028391Notes

Reaction equation

Br[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([NH:17][C:18](=O)[CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:19][C:18]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]=1

Participants

Reactant 2

HCID 904Acetanilide

HCID 5550542-Bromo-3-nitropyridine

Product 1

HCID 129252492-Methyl-3-phenyl-3H-imidazo[4,5-b]pyridineYield 53%

Procedure

The title compound was prepared with the analogous procedure described in example 3 using 2-Bromo-3-nitropyridine (101 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as pale yellow viscous oil (55 mg, 53%). 1H NMR (DMSO) δ 2.48 (s, 3 H), 7.24 (dd, 1 H), 7.53-7.63 (m, 5 H), 8.02 (d, 1 H), 8.20 (d, 1 H); 13C NMR δ 14.6, 118.3, 125.9, 127.4, 128.7, 129.3, 134.1, 134.3, 143.0, 148.7, 152.9. HRMS (FAB): cal. for C13H12N3 [M-FH+]: 210.1031; found: 210.1027.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-996a06a1c83545ec90c2e47ed45731d2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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