tert-Butyl 4-oxopiperidine-1-carboxylate → tert-butyl 7-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179351Notes

Reaction equation

HRID 2179351 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([O:9]N)[CH:6]=[CH:7][CH:8]=1.O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1>>[Br:2][C:3]1[CH:8]=[CH:7][C:6]2[C:13]3[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:12]=3[O:9][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 68109253O-(3-bromophenyl)hydroxylamine hydrochloride

Product 1

HCID 68109423tert-butyl 7-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 11%

Procedure

The product of step B was reacted with tert-butyl 4-oxopiperidine-1-carboxylate then Boc protected following the procedure of Example 29, step B to give tert-butyl 7-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (181 mg, 11%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 7.59 (d, J=1.6 Hz, 1H), 7.34 (dd, J=8.3 Hz, 1.8 Hz, 1H), 7.26 (d, J=8.1 Hz, 1H), 4.53 (s, 2H), 3.82 (t, J=5.4 Hz, 2H), 2.83 (t, J=5.7 Hz, 2H), 1.52 (s, 9H); ESI MS m/z 352 [M+H]+.

Sources & evidence

ORD record
ord-1346277777934d28bfa6ab342cb9d339
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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