Cesium carbonate → HCID 86725405, compound

HRID 1503865Notes

Reaction equation

HRID 1503865 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:16]2[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1185334-Bromo-2-nitroanisoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-

Product 1

HCID 86725405HCID 86725405, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromo-1-methoxy-2-nitrobenzene (232 mg, 1 mmol), tert-butyl piperazine-1-carboxylate (224 mg, 1.2 mmol), palladium diacetate (23 mg, 1.2 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (93 mg, 0.15 mmol) and cesium carbonate (978 mg, 3 mmol) in 1,4-dioxane (15 mL) was heated at reflux for 16 hours. The mixture was filtered through diatomaceous earth and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 4/1 petroleum ether/ethyl acetate to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  6. washeluting with 4/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-7b00ab7ed9f7451ab71d938d3efe4906
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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