Dichloromethane → 1-(4-fluorophenyl)-4-(4-methylpyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(4-Methylpyrimidin-5-yl)boronic acid hydrochloride	HCID 66664699	—
Reactant	1-(4-Fluorophenyl)-4-iodo-1H-pyrazolo[3,4-B]pyridine	HCID 66668437	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	1-(4-fluorophenyl)-4-(4-methylpyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine	HCID 56603006	220%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Example 3 was prepared according to the general procedure of Example 2. Intermediate 2A (0.32 mmol), potassium carbonate (140 mg, 1.01 mmol), 4-methylpyrimidin-5-ylboronic acid hydrochloride salt (78 mg, 0.45 mmol), NMP (1.0 mL), PdCl2(dppf).CH2Cl2 (45 mg, 0.056 mmol), and deoxygenated water (50 μL) were heated at 100° C. for 4 h to give 37.5 mg (63%) of the title compound as an off white solid. Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 15% Solvent B to 85% Solvent B over 12 min, ret. T=9.3 min. 1H NMR (500 MHz, MeOD) δ ppm 2.36 (s, 3 H) 7.29-7.35 (m, 3 H) 7.54 (d, J=5.19 Hz, 1 H) 8.10 (s, 1 H) 8.26-8.32 (m, 2 H) 8.55 (s, 1 H) 8.57 (d, J=5.19 Hz, 1 H) 8.74 (d, J=4.58 Hz, 1 H). LC/MS (Condition B): ret. T=1.82 min, (M+H)+ 305.09. Analytical HPLC: (Condition A): >99%, ret. T=23.46 min, (Condition B): >99%, ret. T=23.49 min, (Condition C): >98%, ret. T=10.4 min, (Condition D): >98%, ret. T=10.6 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08673922B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-503e296b619741fba9d63374147aea48
Source note	uspto-grants-2014_03