2-Methylindole-3-carboxaldehyde

Brown powder

General procedure: POClGeneral procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (NaAnhydrous N, N-dimethylformamide (DMF) (12.6 mL, 163.4 mmol) was placed in an NFormylation of 2-methy-indole was carried out according to McNabFormylation of 2-methy-indole was carried out according to McNabGeneral procedure: To a dried two-neck round-bottom flask containing DMF (0.7mL for 1.10mmol of starting material) chilled in an ice bath, POClGeneral procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv), TMEDA (75 µL, 0.5 mmol, 2.5 equiv), NaGeneral procedure: Water (20mL) was added to a suspension of the iminium salt (Im1, 2, 4, 5), prepared as above. After stirring at 60°C for 15min, the reaction mixture was cooled to rt and then extracted three times with dichloromethane (15mL). The aqueous phase (pH about 3–4), on treatment with 4M NaOH (10mL) releases basic vapours of dimethylamine. The organic layer was washed with brine (15mL×3) and 1M Na

Reactant for preparation of:• ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1• ;Fluorescent sensors (BODIPY)2• ;Antimicrobial agents against methicillin-resistant Staphylococcus aureus3• ;G protein-coupled receptor CRTh2 antagonists4• ;Inhibitors of PI3 kinase-α5• ;Antitubercular agents6• ;Anti-inflammatory agents7• ;Mycobacterium tuberculosis protein tyrosine phosphatase B8• ;Glucocorticoid receptor ligands9• ;Agents stimulating neurite outgrowth10

Molecular Weight:159.18
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:159.068413911
Monoisotopic Mass:159.068413911
Topological Polar Surface Area:32.9
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes