Cesium carbonate → HCID 18980136, compound

HRID 869840Notes

Reaction equation

HRID 869840 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:42]1[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[CH:45]=[CH:44][C:43]=1[O:51][CH3:52].[CH3:53][NH:54][CH2:55][CH2:56][N:57]([CH3:59])[CH3:58]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:52][O:51][C:43]1[CH:44]=[CH:45][C:46]([N+:48]([O-:50])=[O:49])=[CH:47][C:42]=1[N:54]([CH3:53])[CH2:55][CH2:56][N:57]([CH3:59])[CH3:58]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 788702-Bromo-4-nitroanisoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 18980136HCID 18980136, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried flask was charged with cesium carbonate (2.28 g, 7 mmol, 1.4 eq), Pd(OAc)2 (79 mg, 0.35 mmol, 0.07 eq), and X-phos (238 mg, 0.5 mmol, 0.1 eq) under nitrogen. 2-bromo-1-methoxy-4-nitrobenzene (1.16 g, 5 mmol, 1 eq), N1, N2, N2-trimethylethane-1,2-diamine (613 mg, 6 mmol, 1.2 eq) and toluene (20 mL, 0.25 M) were added, and the mixture was heated to 100° C. with stirring overnight. The reaction mixture was cooled to room temperature and concentrated. The crude product was then purified by flash chromatography on silica gel to give N1-(2-methoxy-5-nitrophenyl)-N1, N2, N2-trimethylethane-1,2-diamine (2) (340 mg, 1.34 mmol, 27%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was then purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8edbe109ebcf42618adc20ae826192bc
Source dataset
uspto-grants-2015_03
Patent number
US08969396B2

Reaction notes

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