Dimethyl Sulfoxide → HCID 118093956, compound

HRID 1056970Notes

Reaction equation

HRID 1056970 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O.[NH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 4082852-MorpholinoethylamineHCID 118093763HCID 118093763, compound

Product 1

HCID 118093956HCID 118093956, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1-bromo-4-fluoro-3-nitro-2-phenoxybenzene (0.057 g, 0.18 mmol) and cesium carbonate (0.0715 g, 0.220 mmol) in dimethyl sulfoxide (0.20 mL, 2.8 mmol) was treated with N-(2-aminoethyl)morpholine (0.0289 mL, 0.220 mmol) and stirred at 20° C. for 24 h, after which time the reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 100% EtOAc) gave the desired product (60 mg, 78%) a brown oil. LCMS calculated for C18H21BrN3O4 (M+H)+: m/z=422.1, 424.1. found: 422.1, 424.1.

Workup

  1. customLayers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customPurification by flash column chromatography (100% hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-a219e17b2a9a43b1ad34107382dede6b
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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