Trifluoroacetic acid → 6-bromo-1-isopropyl-1H-imidazo[4,5-c]pyridine

HRID 1778023Notes

Reaction equation

HRID 1778023 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:9][CH:10]([CH3:12])[CH3:11])[CH:3]=1.[CH2:13](OC(OCC)OCC)C.C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[CH:13][N:9]([CH:10]([CH3:12])[CH3:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31214Ethyl orthoformateHCID 901766496-bromo-N4-isopropylpyridine-3,4-diamine2×

Product 1

HCID 901777606-bromo-1-isopropyl-1H-imidazo[4,5-c]pyridine

Conditions

Temperature
125 °C

Procedure

A mixture of 6-bromo-N4-isopropylpyridine-3,4-diamine (intermediate 257, 1.2 g, 5.22 mmol), triethylorthoformate (26.6 ml, 156 mmol) and TFA (0.24 ml, 3.12 mmol) was heated at 125° C. for 3.5 h and then concentrated. The residue was diluted with sat. aq. NaHCO3 and extracted with

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with sat. aq. NaHCO3
  3. extractionextracted with

Sources & evidence

ORD record
ord-724fcb968a834c679e5bafe06f0355d6
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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