Cesium carbonate → HCID 59392794, compound

HRID 216720Notes

Reaction equation

HRID 216720 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][C:18]1([CH3:30])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:25]2[CH:26]=[N:27][NH:28][CH:29]=2)[O:19]1>CN(C=O)C>[CH3:17][C:18]1([CH3:30])[C:22]([CH3:23])([CH3:24])[O:21][B:20]([C:25]2[CH:29]=[N:28][N:27]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[CH:26]=2)[O:19]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 958344-(3-Chloropropyl)morpholineHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59392794HCID 59392794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-Chloro-propyl)-morpholine (702 mg, 4.2 mmol), Cs2CO3 (753 mg, 2.31 mmol) and 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (832 mg, 4.2 mmol) in 5 ml dry DMF are heated at 80° C. under argon for 24 h and then allowed to cool to RT. DMF is removed under HV and the residue is re-taken in EtOAc and washed with de-ionized water. The aqueous phase is re-extracted with EtOAc and the combined organic extracts are washed with saturated brine, dried over Na2SO4, filtered and concentrated under vacuum to dryness. After drying under HV, the title compound is obtained as a pale orange oil, Rt=0.728 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 322 (M+1)+.

Workup

  1. customDMF is removed under HV
  2. washwashed with de-ionized water
  3. extractionThe aqueous phase is re-extracted with EtOAc
  4. washthe combined organic extracts are washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum to dryness
  8. customAfter drying under HV

Sources & evidence

ORD record
ord-f0a17117ebb0420fb776eb5f8313b686
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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