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

HRID 2179336Notes

Reaction equation

HRID 2179336 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[O:10]N.O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>>[Cl:2][C:3]1[C:4]2[O:10][C:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]=3[C:5]=2[CH:6]=[C:7]([Br:9])[CH:8]=1

Participants

3

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 68109187O-(2-chloro-4-bromophenyl)hydroxylamine hydrochloride

Product 1

HCID 68109024tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 20%

Procedure

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).

Workup

  1. customPurification by flash column chromatography (SiO2, 95:5 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6523135861244b118872876eb5a68e6c
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…