Acetic Acid → 6-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 1749807Notes

Reaction equation

HRID 1749807 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[C:11](O)(=[O:13])C.C1N2CN3CN(C2)CN1C3>O>[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10]([CH:11]=[O:13])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 111599156-Bromo-7-azaindole

Product 1

HCID 184006656-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehydeYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

6-Bromo-1H-pyrrolo[2,3-b]pyridine (0.028 g, 0.14 mmol) was successively added with acetic acid (0.1 mL), water (0.2 mL), and hexamethylenetetramine (0.028 g, 0.20 mmol), and then the mixture was stirred overnight at 120° C. in a sealed tube. The reaction mixture was added with water, and the precipitated solid was collected by filtration to obtain 6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.008 g, 25%).

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-54e04f4ed5f144b7826a660df3b6b91a
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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