1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-, Methyl ester synthesis
- Product Name:1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-, Methyl ester
- CAS Number:1228551-75-4
- Molecular formula:C10H9BrN2O2
- Molecular Weight:269.09
67-56-1
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![5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine](/CAS2/GIF/1111638-02-8.gif)
1111638-02-8
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76-02-8
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Yield:1228551-75-4 88%
Reaction Conditions:
Stage #1: 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine;aluminum (III) chloride in dichloromethane; for 0.833333 h;
Stage #2: trifluoroacetyl chloride in dichloromethane; for 18 h;
Stage #3: methanol
Steps:
Step 4 : 5-Bromo-2-methyl-lH-pyrr -blpyridine-3-carboxylic acid methyl esterAluminium trichloride (179 g, 1.34 mol) was added to a mixture of 5-bromo-2-methyl- lH-pyrrolo[2,3-b]pyridine (81 g, 384 mmol) in dichloromethane (1.5 L) and stirred for 50 minutes. Trichloroacetyl chloride (238 g, 147 mL, 1.31 mol) was added and the reaction mixture was left to stir for 18 hours. The reaction mixture was cooled to 0 °C and quenched by the addition of methanol (500 mL). The solvent was evaporated and the resultant residue treated with a mixture of potassium hydroxide (320 g) in methanol (2 L) (caution - exotherm) and the reaction mixture then heated under reflux for 3 hours. The reaction mixture was allowed to cool to ambient temperature then evaporated. The resultant residue was treated with 2M hydrochloric acid to give an acidic mixture. The resulting mixture was extracted with ethyl acetate (x 5), the combined organic layer dried (Na2S04), filtered and evaporated then triturated with diethyl ether to afford the title compound as a buff solid (91 g, 88%). NMR (300 MHz, DMSO-d6): 12.63 (s, 1H), 8.31 (s, 2H), 3.83 (s, 3H), 2.68 (s, 3H).
References:
WO2011/73263,2011,A1 Location in patent:Page/Page column 79-80
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