Cesium carbonate → HCID 86730188, compound

HRID 1850157Notes

Reaction equation

HRID 1850157 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][S@@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH3:9])=[C:4]([F:17])[CH:3]=1.[CH:18]1([B-](F)(F)F)[CH2:20][CH2:19]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2.[Al]>[NH4+].[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[CH:18]1([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][S@@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH3:9])=[C:4]([F:17])[CH:3]=2)[CH2:20][CH2:19]1

Participants

10

Reactant 5

HCID 10796Cesium carbonateHCID 5359268AluminumHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 23697338Potassium cyclopropyltrifluoroborateHCID 86730183(R)-N-((S)-1-(4-bromo-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86730188HCID 86730188, compoundYield 106.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial containing a stir bar was added (R)—N—((S)-1-(4-bromo-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (100 mg, 0.31 mmol) followed by the addition of potassium cyclopropyltrifluoroborate (459 mg, 3.10 mmol), cesium carbonate (506 mg, 1.55 mmol) and Pd(OAc)2 (7 mg, 0.03 mmol) and di(1-adamantyl)-n-butylphosphine (22 mg, 0.06 mmol), toluene (2.6 mL) and finally water (0.5 mL). The vial capped and heated by microwave irradiation for 20 min at 100° C., followed by thermal heating at 100° C. in a preheated aluminum tray for 18 hours. The reaction mixture was diluted with a saturated solution of NH4Cl. The aqueous mixture extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to afford a yellow crystalline of (R)—N—((S)-1-(4-cyclopropyl-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (116 mg, 0.33 mmol, 106% yield). LCMS m/z 284.0 (M+H)+, Rt 0.90 min.

Workup

  1. additionTo a microwave vial containing a stir bar
  2. customThe vial capped
  3. extractionThe aqueous mixture extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-867506725c25429da721aca0984f0209
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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