Methanol → methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochloride
Reaction equation
Cl.[NH:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4]=[C:3]1[C:11]([OH:13])=[O:12].S(Cl)([Cl:16])=O.[CH3:18]O>>[ClH:16].[NH:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4]=[C:3]1[C:11]([O:13][CH3:18])=[O:12]Participants
4
Procedure
To a solution of 4 g of 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid hydrochloride in 100 mL of methanol are added dropwise 6 mL of thionyl chloride at room temperature. The reaction mixture is then stirred for 5 hours at room temperature, and then concentrated under reduced pressure. The residue obtained is triturated in 50 mL of ethyl ether and then dried under vacuum at 40° C. 3.22 g of methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochloride are obtained in the form of a pale yellow solid, which is used in unmodified form in the following step.
Workup
- concentrationconcentrated under reduced pressure
- customThe residue obtained
- customis triturated in 50 mL of ethyl ether
- customdried under vacuum at 40° C
Sources & evidence
- ORD record
- ord-8c15762c5fa944b3bd48cb2f5c1c62a1
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947706B2
Reaction notes
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