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

5-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

1111638-01-7

1111638-02-8

Preparation of Method A Steps for the synthesis of intermediate 4: 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine: Ingredient 3 (88 mg, 0.251 mmol) was dissolved in methanol (4 mL), 2 N sodium hydroxide solution (1 mL) was added, and the reaction mixture was heated and refluxed for 2 hours. After completion of the reaction, ethyl acetate was added for extraction and the organic phase was washed sequentially with 1 N sodium hydroxide solution and water. Purification by silica gel column chromatography (slow gradient elution, volume fraction of methanol in dichloromethane increased from 0% to 2%) afforded the target product 4 (40 mg, 0.19 mmol, 76% yield). Product characterization data were as follows: 1H NMR (CDCl3, 300 MHz): δ 10.26 (br s, 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).

1312755-43-3 Synthesis

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

1312755-43-3
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1111638-02-8
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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

1111638-01-7
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1111638-02-8
117 suppliers
$19.00/100mg

References

183208-35-7 Synthesis