Related Products of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
6-Nitroindoline (1. 2 MMOL) was dissolved in DCM (8 ML), treated with pyridine (2. 4 MMOL) and cooled to 0C. MESO2CI (1. 3 mmol) was added dropwise and the mixture allowed to stir at room temperature overnight. 0. 5 M HCI solution (10 ML) was added and the mixture extracted twice with DCM (10 ml) and twice with EtOAc (10 ML). The combined organics were washed with brine, dried over NA2SO4 and evaporated. The dried residue was dissolved in MeOH (5 ml) and THF (4 ml). Pd/C (100 mg) was added and the mixture stirred under an atmosphere of hydrogen at room temperature for 5 h. The mixture was filtered through a pad of Celite, which was washed with plenty of MeOH and EtOAc. The filtrate was concentrated in vacuum and the residue dried. The crude 6-amino indoline derivative and 4, 6-dichloropyrimidine (1. 5 MMOL) were dissolved in isopropanol (6 ml) and conc. HCI (0. 4 ml) and the mixture heated to reflux for 2. 5 h. For precipitation of the intermediate product the mixture was stored in the fridge overnight. The precipitate (HCI salt) was filtered, washed with a small quantity of cold isopropanol and dried. The intermediate (0. 17 MMOL), the corresponding phenylboronic acid (0. 2 mmol), Na2CO3 (0. 58 mmol) and Pd (PPh3) 2CI2 (3 mol%) were suspended in a mixture of DME/ETOH/WATER (1. 5 ML/0. 3 ML/0. 2 ML). The mixture was heated in the microwave at 125C for 1200 s. H20 (30 ml) was added and the mixture extracted twice with EtOAc (40 ML). Saturated NH4CI solution (20 ml) was added to the water phase and extracted again twice with EtOAc (40 ml). The combined organics were washed with brine and dried over NA2SO4. After evaporation of the solvent the residue was taken up in DMSO and purified via prep.-HPLC (XTerra Prep. MS C18 5 um, 19 X 150 mm, gradient from water to MeCN over 13 min).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Nitroindoline, its application will become more common.
Reference:
Patent; AXXIMA PHARMACEUTICALS AG; WO2005/26129; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem