Cesium carbonate → HCID 22736995, compound

HRID 51888Notes

Reaction equation

HRID 51888 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.Cl.[CH3:14][NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:15]([CH3:14])[CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1185334-Bromo-2-nitroanisoleHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 22737007Methyl((oxan-4-yl)methyl)amine hydrochloride

Product 1

HCID 22736995HCID 22736995, compoundYield 62.4%

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 4.70 g (20.0 mmol) 4-bromo-2-nitro-anisole in 100 ml dioxane were added 4.03 g (24.3 mmol) methyl-(tetrahydro-pyran-4-ylmethyl)-amine hydrochloride (1:1), 0.710 g (20.0 mmol) 2-(dicyclohexylphosphino)biphenyl, 16.5 g (50.65 mmol) cesium carbonate, and 227 mg (1.0 mmol) palladium (II) acetate. The mixture was heated at reflux for 24 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 hexane/ethyl acetate) afforded 3.5 g (62%) (4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-ylmethyl)-amine as a red oil. ES-MS m/e (%): 281 (M+H+, 100).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. additionpoured onto water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4548c2d968b40179f8332165ab7fea2
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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