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ChemicalBook CAS DataBase List 1H-Pyrrolo[2,3-b]pyridine, 5-broMo-2,3-diMethyl-
145934-65-2

1H-Pyrrolo[2,3-b]pyridine, 5-broMo-2,3-diMethyl- synthesis

6synthesis methods
1H-Pyrrolo[2,3-b]pyridine, 5-broMo-2,3-diMethyl-1-(phenylsulfonyl)-

1111637-98-9
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1H-Pyrrolo[2,3-b]pyridine, 5-broMo-2,3-diMethyl-

145934-65-2
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Yield:145934-65-2 72.4%

Reaction Conditions:

with methanol;sodium hydroxide;water in tetrahydrofuran at 20;Heating / reflux;

Steps:

B-6

Preparation of 5-bromo-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridine (B-6-4)B-6-3 β-6-4To a suspension of 5-bromo-2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-3) (0.9 g, 2.5 mmol) in THF (30 mL) and MeOH (30 mL) was added aq. NaOH (20%, 19 mL) at room temperature. The mixture was heated to reflux overnight. TLC (Petroleum ether: EtOAc = 5:1 ) showed the reaction was complete. After the solvent was removed under reduced pressure, water (20 mL) and CH2CI2 (20 mL) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4. The mixture was concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2,3- dimethyl-1 H-pyrrolo[2,3-b]pyridine (B-6-4) (0.4 g, 72.4%) as a white solid.

References:

WO2009/16460,2009,A2 Location in patent:Page/Page column 70-71