1-Fluoro-4-(2-nitroethenyl)benzene → 1-Benzyl-3-(4-fluoro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 749712Notes

Reaction equation

HRID 749712 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][N+:24]([O-])=O)=[CH:18][CH:17]=1>C(N)C1C=CC=CC=1>[CH2:22]([N:24]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)=[CH:23]1)[C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 983991-Fluoro-4-(2-nitroethenyl)benzeneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 533231151-Benzyl-3-(4-fluoro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

The title compound (706.2 mg) was prepared from 1.31 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 700 μL of benzylamine, and 1.10 g of 1-fluoro-4-(2-nitro-vinyl)-benzene. MS (ESI): exact mass calculated for C20H19FN2, 306.15; found, m/z 307.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.36-7.25 (m, 5H), 7.18-7.15 (m, 2H), 7.11-7.05 (m, 3H), 5.13 (s, 2H), 4.33 (s, 2H), 3.50 (t, J=6.3 Hz, 2H), 2.86 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record
ord-fbd00b8f120f4bed9972b2f12e96c9aa
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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