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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2179336Generated: October 29, 2026

tert-Butyl 4-oxopiperidine-1-carboxylate → tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

https://huagongshe.com/reaction/2179336

Reaction equation

Participants

RoleNameHCIDCharge
Reactanttert-Butyl 4-oxopiperidine-1-carboxylateHCID 735900—
ReactantO-(2-chloro-4-bromophenyl)hydroxylamine hydrochlorideHCID 68109187—
Producttert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateHCID 6810902420%

Reaction Steps

The product of step A was reacted with tert-butyl 4-oxopiperidine-1-carboxylate then Boc protected following the procedure of Example 29, step B. Purification by flash column chromatography (SiO2, 95:5 hexanes/ethyl acetate) provided tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (3.9 g, 20%) as a pink solid: 1H NMR (CDCl3, 300 MHz) δ 7.44 (d, J=1.5 Hz, 1H), 7.38 (d, J=1.5 Hz, 1H), 4.50 (s, 2H), 3.88 (t, J=5.4 Hz, 2H), 2.89 (t, J=5.4 Hz, 2H), 1.49 (s, 9H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09067949B2
Source datasetuspto-grants-2015_06
ORD IDord-6523135861244b118872876eb5a68e6c
Source noteuspto-grants-2015_06