ChemicalBook CAS DataBase List 5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE

5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE synthesis

7synthesis methods

Product Name:5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE
CAS Number:4943-67-3
Molecular formula:C8H8N2
Molecular Weight:132.16

65156-94-7 Synthesis

65156-94-7
143 suppliers
$18.00/100mg

823-96-1
191 suppliers
$47.00/5G

4943-67-3
44 suppliers
$60.00/2mg

Yield:4943-67-3 55%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium carbonate in monoethylene glycol diethyl ether at 120; for 1 h;Inert atmosphere;Microwave irradiation;

Steps:

20 PREPARATION 20 5-Methyl-1 H-pyrrolo[3,2-fe]pyridine

PREPARATION 20 5-Methyl-1 H-pyrrolo[3,2-fe]pyridine The title compound of Preparation 19 (200 mg, 1 .31 mmol), trimethylboroxine (0.20 ml, 1 .44 mmol) and potassium carbonate (540 mg, 3.93 mmol) were suspended in 5 ml 1 ,2-dimethoxyethane in a microwave reactor and the mixture was submitted to three vacuum-argon cycles. [1 , 1 '-Bis(diphenylphosphino)ferrocene]dichloropalladium (I I), complex with dichloromethane (53 mg, 0.07 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The reaction was stirred at 120 °C for 1 h under microwave irradiation. The reaction was allowed to cool, diluted with ethyl acetate and water and filtered through Celite eluting with more ethyl acetate and water. The organic extract was washed with brine, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The resulting residue was purified using the Isolera Purification System (methanol-dichloromethane gradient, 0: 100 rising to 5:95) to give 95 mg (0.72 mmol, 55%) of the title compound as an oil. Purity 96%. ¹ H N MR (300 MHz, CHLOROFORM-d) δ ppm 8.44 (br. s., 1 H), 7.60 (d, J=8.24 Hz, 1 H), 7.41 (t, J=3.02 Hz, 1 H), 7.01 (d, J=8.24 Hz, 1 H), 6.69 (br. s., 1 H), 2.67 (s, 3 H). UPLC/MS (3 min) retention time 0.45 min. LRMS: m/z 133 (M+1 ).

References:

WO2013/10880,2013,A1 Location in patent:Page/Page column 83-84

400777-06-2 Synthesis