ChemicalBook CAS DataBase List 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine synthesis

6synthesis methods

Product Name:5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine
CAS Number:1111638-02-8
Molecular formula:C8H7BrN2
Molecular Weight:211.06

1312755-43-3 Synthesis

2-PyridinaMine, 5-broMo-3-(1-propyn-1-yl)-

1312755-43-3
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5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

1111638-02-8
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$19.00/100mg

Yield: 97%

Reaction Conditions:

with potassium tert-butylate in tert-butyl alcohol at 85; for 1 h;

Steps:

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 (Na₂S0₄) and evaporated then triturated with diethyl ether to afford the title compound as a brown solid (88.7 g, 97%). NMR (400 MHz, CDC1₃): 10.21 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 7.91 (d, J = 2.1 Hz, 1H), 6.13 (s, 1H),2.52 (s, 3H).

References:

F. HOFFMANN-LA ROCHE AG;DYKE, Hazel Joan;GAZZARD, Lewis J.;WILLIAMS, Karen WO2011/73263, 2011, A1 Location in patent:Page/Page column 79