2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178452509, compound

HRID 1751339Notes

Reaction equation

HRID 1751339 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH2:25][CH2:26][C:16]=3[N:15]=2)=[CH:23][C:22]([Br:27])=[CH:21][CH:20]=4)[C@@H:12]2[CH2:28][C@H:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH:25]=[CH:26][C:16]=3[N:15]=2)=[CH:23][C:22]([Br:27])=[CH:21][CH:20]=4)[C@@H:12]2[CH2:28][C@H:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178452512HCID 178452512, compound

Product 1

HCID 178452509HCID 178452509, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(1R,3S,4S)-tert-butyl-3-(7-bromo-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1.25 g, 2.81 mmol) was diluted in benzene (50 mL). DDQ (0.7 g, 3.1 mmol) was added and the solution was heated to reflux for 1.5 h. After cooling, the reaction mixture was concentrated and the residue was purified by silica gel chromatography to yield product (1.1 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 1.5 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d7d86ed3bc4f489fa20baeb1d3828f40
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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