ethyl 4-(5-bromo-3-nitropyridin-2-yl)tetrahydro-2H-pyran-4-carboxylate → 6'-Bromo-1',2'-dihydrospiro[oxane-4,3'-pyrrolo[3,2-b]pyridine]-2'-one

HRID 1618521Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[C:5]([C:8]2([C:14](OCC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1>[Fe].CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[NH:19][C:14](=[O:15])[C:8]3([CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared according to procedure J using ethyl 4-(5-bromo-3-nitropyridin-2-yl)tetrahydro-2H-pyran-4-carboxylate (250 mg, 0.724 mmol), AcOH (4 mL) and Fe powder (202 mg, 3.62 mmol) and heating the mixture at 100° C. for 2 h. After purification 6′-bromo-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-2′(1′H)-one was obtained.

Workup

customPrepared
customAfter purification 6′-bromo-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-2′(1′H)-one
customwas obtained

Sources & evidence

ORD record: ord-fca46595b7294c739f4f8701a85b0dc8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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