HCID 68157050, compound → HCID 68157725, compound

HRID 243200

Reaction equation

HRID 243200 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:6]=1[CH:15]=[CH2:16])C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[F:14][C:7]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:5]2[C:6]=1[CH:15]=[CH:16][CH2:1][NH:4]2

Participants

4

Reactant 1

HCID 68157050HCID 68157050, compound

Product 1

HCID 68157725HCID 68157725, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of allyl-(3-fluoro-6-nitro-2-vinylphenyl)amine (109 mg, 0.49 mmol) in DCM (10 mL) was added Grubbs catalyst (2nd generation, benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium) (8.5 mg, 0.01 mmol). The reaction mixture was stirred at RT for 16 h, and then purified by column chromatography (Si—PCC, eluant DCM) affording the title compound as a red solid (83.6 mg, 88%). 1H NMR (CDCl3, 300 MHz): 8.17 (1H, bs), 7.88 (1H, dd, J=9.6, 6.0 Hz), 6.52 (1H, dt, J=10.3, 2.2 Hz), 6.22 (1H, dd, J=9.7, 8.3 Hz), 5.77-5.71 (1H, m), 4.55-4.52 (2H, m)

Workup

  1. custompurified by column chromatography (Si—PCC, eluant DCM)

Sources & evidence

ORD record
ord-4984fd35999d41cfb7ba420ada916145
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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