Acetic Acid → 3,3-dimethyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

HRID 1618536Notes

Reaction equation

[CH3:1][C:2]([C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:10][N:9]=1)([CH3:7])[C:3](OC)=[O:4].C(O)(=O)C>[Fe]>[CH3:1][C:2]1([CH3:7])[C:8]2=[N:9][CH:10]=[C:11]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[C:13]2[NH:14][C:3]1=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)-propanoate (1.2 g, 3.88 mmol) in acetic acid (22.2 mL, 388 mmol) was added iron powder (1.08 g, 19.40 mmol). The reaction was heated at 80° C. for 2 h. After this time the reaction was cooled to rt and filtered over Celite™. The Celite™ was washed with acetic acid and the combined filtrates were evaporated in vacuo. Purification by column chromatography (hexane:EtOAc, 1:0 to 0:1) gave 3,3-dimethyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-2(3H)-one. Mass Spectrum (ESI) m/e=248 (M+1).

Workup

temperatureAfter this time the reaction was cooled to rt
filtrationfiltered over Celite™
washThe Celite™ was washed with acetic acid
customthe combined filtrates were evaporated in vacuo
customPurification by column chromatography (hexane:EtOAc, 1:0 to 0:1)

Sources & evidence

ORD record: ord-72782e3da8c04aa2934a842f069516d8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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