Hydrochloric Acid → benzyl 1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 844443Notes

Reaction equation

C([Li])(C)(C)C.[C:6]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20])(OC(C)(C)C)=O.[C:21]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])C([O-])=O.Cl.[OH-].[Na+]>CCCCC.C1COCC1>[NH:13]1[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[CH:20]=[C:6]1[C:21]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]

Participants

Conditions

Temperature: -40 °C

Procedure

40 ml of 1.7M tert-butyllithium in pentane are added, at −40° C. under nitrogen, to 5 g of 4-(N-Bocamino)-3-methylpyridine. After stirring for 1 hour at −40° C., the lithiated derivative thus formed is added to 12.9 g of benzyl oxalate in 100 ml of THF at −40° C. The mixture is allowed to return to 0° C., it is left stirring for 2 hours, 25 ml of 6N HCl are then added and this mixture is heated at 50° C. for one and a half hours. The pH is brought to 9 by addition of 1N NaOH, the mixture is then extracted with EtOAc and the extracts are dried and evaporated. The residue is chromatographed on silica, eluting with DCM/MeOR (100/3; v/v) to give 2.7 g of the expected compound.

Workup

customthe lithiated derivative thus formed
customto return to 0° C.
waitit is left
stirringstirring for 2 hours
temperaturethis mixture is heated at 50° C. for one and a half hours
extractionthe mixture is then extracted with EtOAc
customthe extracts are dried
customevaporated
customThe residue is chromatographed on silica
washeluting with DCM/MeOR (100/3; v/v)

Sources & evidence

ORD record: ord-7407aa4c38a749dd8bf6c668938032d6
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380230B1

Reaction notes

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