Propionic Acid → HCID 178437391, compound

HRID 1469112Notes

Reaction equation

HRID 1469112 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10](O)(=O)[CH2:11][CH3:12]>>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:10]([CH2:11][CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 1032Propionic AcidHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 178437391HCID 178437391, compoundYield 45%

Procedure

4 g of 5-bromopyridine-2,3-diamine in 40 ml of propionic acid is heated at 140° C. in a flask until the diamine has reacted completely (HPLC check, about 24 hours). The cooled reaction solution is evaporated to dryness. The residue is suspended in water, filtered off with suction and purified by means of column chromatography (gradient EA: methanol 5-40% in 30 min), giving 2.25 g of 6-bromo-2-ethyl-3H-imidazo[4,5-b]pyridine as yellowish solid (yield 45%, content 98%); MS-FAB (M+H+)=228.0; Rf (polar method): 1.27 min.

Workup

  1. customhas reacted completely (HPLC check, about 24 hours)
  2. customThe cooled reaction solution
  3. customis evaporated to dryness
  4. filtrationfiltered off with suction
  5. custompurified by means of column chromatography (gradient EA: methanol 5-40% in 30 min)

Sources & evidence

ORD record
ord-118ff2ef66494cc287cc9e1392e7869a
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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