Morpholine → HCID 59631412, compound

HRID 1431749Notes

Reaction equation

HRID 1431749 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[O:18]1[CH2:19][CH2:20][N:15]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 239341Methyl 3-bromo-5-nitrobenzoateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 59631412HCID 59631412, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of methyl 3-bromo-5-nitrobenzoate (5 g, 19.23 mmol), morpholine (1.76 mL, 20.19 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.32 g, 1.442 mmol), XPhos (1.38 g, 2.88 mmol), tripotassium phosphate (5.71 g, 26.9 mmol), and toluene (38.5 mL) was stirred overnight at 95° C. under nitrogen. Upon completion, the reaction was cooled to 23° C. and filtered over Celite. The filtrate was concd, and the crude material was purified by column chromatography (silica; 0-30% EtOAc in hexanes) to afford methyl 3-morpholino-5-nitrobenzoate as an orange amorphous solid. Mass Spectrum (ESI) m/e=267.2 (M+1).

Workup

  1. temperatureUpon completion, the reaction was cooled to 23° C.
  2. filtrationfiltered over Celite
  3. customthe crude material was purified by column chromatography (silica; 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b92a876e97844e3eaf8c1b7c23d3b20d
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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