methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate → 6-Bromo-1,2-dihydrospiro[indole-3,4'-oxane]-2-one

HRID 1618488Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14](OC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:4]([N+:18]([O-])=O)[CH:3]=1>[Fe].CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[NH:18][C:14](=[O:15])[C:8]3([CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[C:5]2=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared according to procedure J using methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (6.67 g, 19.4 mmol), AcOH (97 mL) and Fe powder (5.42 g, 96.97 mmol) and heating the mixture at 100° C. for 2 h. After purification 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one was obtained as an orange solid. Mass Spectrum (ESI) m/e=282 [(M+1) (79Br)] and 284 [(M+1) (81Br)].

Workup

customPrepared
customAfter purification 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one
customwas obtained as an orange solid

Sources & evidence

ORD record: ord-543ce9ca53074e4fb0d2bf197cfc781e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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