Cesium carbonate → HCID 68672005, compound

HRID 2047383Notes

Reaction equation

HRID 2047383 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH:13]([F:15])[F:14])[C:11]3[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:20](=[O:23])([O-])[O-].[Cs+].[Cs+].C1(P([C:66]2[CH:71]=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:72]([N:75]1[CH2:81][CH2:80][CH2:79][NH:78][CH2:77][CH2:76]1)(=[O:74])[CH3:73]>C1(C)C=CC=CC=1>[F:14][CH:13]([F:15])[N:12]1[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[N:9]=[C:8]1[C:4]1[CH:3]=[C:2]([N:9]2[CH2:66][CH2:71][N:12]([C:20]([N:78]3[CH2:79][CH2:80][CH2:81][N:75]([C:72](=[O:74])[CH3:73])[CH2:76][CH2:77]3)=[O:23])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 4186202N-AcetylhomopiperazineHCID 59568376HCID 59568376, compound

Product 1

HCID 68672005HCID 68672005, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

2-(3-Bromo-phenyl)-1-difluoromethyl-1H-benzoimidazole (0.10 g, 0.31 mmol), cesium carbonate (0.14 g, 0.43 mmol), rac-2,2′ bis(diphenylphosphino)-1,1′-binaphtyl (BINAP) (0.007 g, 0.01 mmol) and tris-(dibenzilideneacetone)-dipalladium(0) (0.004 g) were placed into a 7 mL sealed vial and purged by repeated nitrogen/vacuum cycles for ten minutes. Dry toluene (0.6 mL) and N-acetylhomopiperazine (0.05 mL, 0.37 mmol) were added and reaction mixture was heated at 85° C. for 24 hours with stirring.

Workup

  1. customsealed vial
  2. custompurged by repeated nitrogen/vacuum cycles for ten minutes
  3. customreaction mixture

Sources & evidence

ORD record
ord-5c617eba242440e9ab07f1d6b5296a16
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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