Acetic Acid → 6-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

HRID 1749820Notes

Reaction equation

[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[CH:11][C:6]2=[CH:5][CH:4]=1)#[CH:2].[C:12](O)(=[O:14])C.C1N2CN3CN(C2)CN1C3.C(=O)([O-])O.[Na+]>O>[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[C:11]([CH:12]=[O:14])[C:6]2=[CH:5][CH:4]=1)#[CH:2]

Participants

Conditions

Temperature: 120 °C

Procedure

6-Ethynyl-1H-pyrrolo[2,3-b]pyridine (0.016 g, 0.11 mmol) was successively added with acetic acid (0.1 mL), water (0.2 mL), and hexamethylenetetramine (0.023 g, 0.17 mmol), and then the mixture was stirred overnight at 120° C. in a sealed tube. The reaction mixture was cooled to room temperature, and then added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 6-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.016 g, 85%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-cb5c346b0bfe420e82b0945bdbf30fcb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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