2-Methyl-5-bromo-7-azaindole

Preparation of Method A Intermediate 4: 5-Bromo-2-methyl-lH-pyrrolo [2, 3-6] pyridine[0427] Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2percent MeOH in DCM), 40 mg (0.19 mmol, 76percent) of 4 is obtained. 1H NMR (CDCls, 300 MHz): δ 10.26 (bs, 1H), 8.22 (d, J= 2.1 Hz, 1H), 8.92 (d, J= 2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H). MS (m/z): 210 (M+H).Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2percent MeOH in DCM), 40 mg (0.19 mmol, 76percent) of 4 is obtained. NMR (CDCITo a solution of compound 19 (1.3 g, 3.7 mmol) in Methynol (MeOH, 85 mL) 2 M of Sodium hydroxide (NaOH) solution (22 mL) was added. Preparation of 5-bromo-2-methyl-1H-pyrrolo[2, 3-b]pyridine (B-7-6)Step 3 : 5-Bromo-2-methyl-lH-pyrrolor2, 3-b1pyridine5-Bromo-3-prop-l-ynyl-pyridin-2-ylamine (91 g, 431 mmol) was treated with a 1M solution of potassium ie/t-butoxide in ie/t-butanol (700 mL) and the reaction mixture was heated at 85 °C for 1 hour. The mixture was then allowed to cool to ambient temperature and poured onto a 1: 1 mixture of water / ice {ca. 1 L). The resultant precipitate was collected by filtration, washed with water and left to air dry. The resultant solid was dissolved in dichloromethane, dried (NaA mixture of 5-bromo-3-prop-i-ynyl-pyridin-2-amine (646 mg, 3.06 mmol), potassium tert-butoxide (558 mg, 4.97 mmol) and 2-methyl-2-propanol (10 mL) was stirred at 85 °C for 20 h. The reaction was diluted with water (30 mL), extracted with ethyl acetate (50 mL x3), dried over Na2504, filtered and concentrated to give 5-bromo-2-methyl-1H-pyrrolo[2, 3- b]pyridine (584 mg, 90percent). LCMS (ESI) [M+H] = 211.0.Under an inert atmosphere, 5-bromo-2-methyl-l//-pyrrolo[2, 3-]pyridine (450 mg, 2.13 mmol), Zn(CN)2 (376 mg, 3.2 mmol) and tetrakis(triphenyiphosphine)palladium(0) (246 mg, 0 213 mmol) were dissolved in l-methylpyrrolidin-2-one (18 mL), and heated at 150 C overnight. After cooling, the reaction mixture was diluted with water, and the product was extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over Xa'SOi and evaporated to dryness. The residue was chromatographed (silica gel, cyclohexane - EtOAc, (6:4)) to give 159 mg (47 %) of 2-methyl4/:/-pyrrolo[2, 3~/>]pyridine~5~earbonitrileA mixture of

Molecular Weight:211.06
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes