Dimethyl Sulfoxide → HCID 86681329, compound

HRID 1430321Notes

Reaction equation

HRID 1430321 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[C:11]12([CH:21]3[CH2:25][CH2:24][CH2:23][NH:22]3)[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C>[C:11]12([CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3[C:6]3[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[C:3]=3[C:4]#[N:5])[CH2:20][CH:15]3[CH2:14][CH:13]([CH2:19][CH:17]([CH2:16]3)[CH2:18]1)[CH2:12]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 511811HCID 511811, compoundHCID 27831392-Bromo-6-fluorobenzonitrile

Product 1

HCID 86681329HCID 86681329, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2-Bromo-6-fluorobenzonitrile (900 mg), 2-adamantan-1-yl-pyrrolidine (924 mg), and potassium carbonate (1244 mg) were added to dimethyl sulfoxide and the mixture was heated at 130° C. for 16 hours. The solution was cooled, diluted with ethyl acetate, washed twice with 1M HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the crude material was concentrated under vacuum and purified on silica gel using 5% ethyl acetate (hexanes) to provide the title compound.

Workup

  1. temperatureThe solution was cooled
  2. washwashed twice with 1M HCl
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe crude material was concentrated under vacuum
  7. custompurified on silica gel using 5% ethyl acetate (hexanes)

Sources & evidence

ORD record
ord-eb353c50cb734996945367307729c865
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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