Diisopropylethylamine → methyl 1-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)piperidine-4-carboxylate

HRID 511504Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14].[NH:16]1[CH2:25][CH2:24][CH:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][N:5]1[CH2:4][C:3]2[C:7](=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=2[N:16]2[CH2:25][CH2:24][CH:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17]2)[C:6]1=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

4-Bromo-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (320.0 mg, 1.180 mmol), methyl isonipecotate (1.595 mL, 11.80 mmol), DIPEA (2.056 mL, 11.80 mmol) and DMF (5 mL) were mixed and heated in sealed tube at 90° C. for 3 days. The crude mixture was purified by MDP under basic conditions to obtain the title compound (33 mg, 8.4% yield). MS (ES+): m/z 334.16 (100) [MH+]; HPLC: tR=0.80 min (UPLC, Analytical).

Workup

customThe crude mixture was purified by MDP under basic conditions

Sources & evidence

ORD record: ord-204126aa154c4f339a13edca47a7ba81
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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