Morpholine → HCID 59165549, compound

HRID 1442535Notes

Reaction equation

HRID 1442535 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:15][S:12]([C:9]1[CH:10]=[CH:11][C:2]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:14])=[O:13]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2517421HCID 2517421, compound

Product 1

HCID 59165549HCID 59165549, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-chloro-5-methanesulfonylbenzoate (23.4 g, 94 mmol) in toluene (250 ml) were added morpholine (9.8 ml, 113 mmol), cesium carbonate (40 g, 122 mmol), palladium acetate (380 mg, 1.4 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.06 g, 1.7 mmol). After stirring overnight with heating under reflux, ethyl acetate (250 ml) was added. The organic layer was washed successively with water (200 ml×2) and saturated brine (200 ml), and dried over magnesium sulfate. Filtration and concentration gave methyl 5-methanesulfonyl-2-(morpholin-4-yl)benzoate as a crude product. The obtained compound was used for Step 4 without further purification.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. washThe organic layer was washed successively with water (200 ml×2) and saturated brine (200 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-f8e805545f9e40d0a26a5465c32b71f5
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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