Ethyl orthoformate → 6-Bromo-4H-imidazo[4,5-b]pyridine

HRID 1848034Notes

Reaction equation

HRID 1848034 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10](OC(OCC)OCC)C>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 9115786-Bromo-4H-imidazo[4,5-b]pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 5-bromopyridine-2,3-diamine (5 g, 26.6 mmol), formic acid (2.5 mL), and triethylorthoformate (70 mL) was heated at 100° C. for 2.5 h. The reaction mixture was cooled to rt and the solid precipitate was collected by filtration, washed with Et2O and dried to afford 6-bromo-3H-imidazo[4,5-b]pyridine as a solid (3.22 g, 61%) which did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H), 8.50 (s, 1H), 8.44 (d, J=2.1 Hz, 1H), 8.31 (d, J=1.9 Hz, 1H). LCMS (ESI) m/z 198 and 200 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationthe solid precipitate was collected by filtration
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-38357718f8ce464ba2b8a4bd2717718f
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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