Cesium fluoride → (3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 1867802Notes

Reaction equation

HRID 1867802 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[C:4]([F:21])[CH:3]=1.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].[F-].[Cs+]>C(#N)C>[F:21][C:4]1[CH:3]=[C:2]([C:29]2[CH:30]=[CH:31][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:27][CH:28]=2)[CH:7]=[CH:6][C:5]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:9]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11965125(4-Bromo-2-fluoro-phenyl)-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Product 1

HCID 57980138(3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Procedure EE: In a microwave reactor vessel, add (4-bromo-2-fluoro-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (1.0 mmol), 4-methanesulfonylphenyl boronic acid (2.5 mmol), dichloropalladium di-triphenylphosphine (0.2 mmol), cesium fluoride (9.0 mmol) and acetonitrile (0.20M) and run in a CEM microwave reactor for 10 minutes at 120° C. with 75W power and cooling on. After this time, wash the reaction with water while extracting with 10% isopropanol/dichloromethane. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 431.2 (M+1)

Workup

  1. temperaturecooling on
  2. washAfter this time, wash
  3. customthe reaction with water
  4. extractionwhile extracting with 10% isopropanol/dichloromethane
  5. dry with materialDry the organic layer with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the title compound via radial chromatography
  9. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-d859029478ef4950ae6ef5546697b465
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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