Cesium carbonate → HCID 66727950, compound

HRID 573303Notes

Reaction equation

HRID 573303 reaction equation
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:36]1[C:40]2=[N:41][CH:42]=[CH:43][CH:44]=[C:39]2[NH:38][CH:37]=1.[CH3:45][O:46][CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52](B2OC(C)(C)C(C)(C)O2)=[CH:51][CH:50]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:45][O:46][CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([C:36]2[C:40]3=[N:41][CH:42]=[CH:43][CH:44]=[C:39]3[NH:38][CH:37]=2)=[CH:51][CH:50]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 179989012-[4-(Methoxymethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 441192133-Bromo-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 66727950HCID 66727950, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of Xphos (0.695 g), 3-bromo-1H-pyrrolo[3,2-b]pyridine (3.59 g), 2-[4-(methoxymethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.81 g) and Cs2CO3 (11.86 g) in DME (50 mL) and water (10 mL) was added Pd2(dba)3 (0.334 g). The mixture was refluxed overnight under Ar atmosphere. The mixture was added to water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column Chromatography (AcOEt/hexane) to give the title compound (0.650 g).

Workup

  1. temperatureThe mixture was refluxed overnight under Ar atmosphere
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column Chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-53ea5eaf701b4b40ba1a1931443945bd
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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