Cesium carbonate → HCID 59392766, compound

HRID 216712Notes

Reaction equation

HRID 216712 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][O:18][C:19]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:20]=1[OH:34]>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:20]=1[O:34][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 958344-(3-Chloropropyl)morpholineHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 59392766HCID 59392766, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-Chloro-propyl)-morpholine (460 mg, 2.75 mmol), Cs2CO3 (493 mg, 1.515 mmol) and 2-Methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (703 mg, 2.75 mmol) in dry DMF (15 ml) 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 solid, Rt=0.878 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: 378 (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-4aaecdbbcadd4752890a99234dcf687e
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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