Water → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1506196Notes

Reaction equation

HRID 1506196 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(O)CO>[CH:13]1([NH:19][C:2]2[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]3[NH:10][CH:11]=[CH:12][C:3]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 867266334-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (845 mg, 4.68 mmol) and cyclohexylamine (2.5 mL, 22 mmol) in ethylene glycol (2 mL) were stirred at 170° C. for 1 hour under microwave irradiation. The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with chloroform. The organic layer was stirred with 2 M hydrochloric acid (20 mL) for 1 hour, and the organic layer was separated. The aqueous layer was adjusted to pH 9 or above with 10 M aqueous sodium hydroxide and extracted with chloroform. The organic layers were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound as a pale yellow oil (804 mg, yield 71%).

Workup

  1. extractionextracted with chloroform
  2. customthe organic layer was separated
  3. extractionextracted with chloroform
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-1af054871d3443118faba8102ddedd65
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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