Cesium carbonate → HCID 89621860, compound

HRID 536466Notes

Reaction equation

HRID 536466 reaction equation
Br[C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([OH:12])[CH2:6]2.[C:13]1([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[NH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]1([C:19](=[N:20][C:2]2[C:10]([F:11])=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([OH:12])[CH2:6]3)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 89621492HCID 89621492, compound

Product 1

HCID 89621860HCID 89621860, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of Example 25E (950 mg, 4.11 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (154 mg, 0.247 mmol), Pd2(dba)3 (11 mg, 0.12 mmol), diphenylmethanimine (1.09 mL, 6.17 mmol) and Cs2CO3 (335 mg, 10.3 mmol) in toluene (20 mL) was heated at 85° C. for 16 hours. The mixture was cooled to ambient temperature, filtered through a layer of Celite, and washed with diethyl ether (60 mL). The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (gradient elution: 0-20% EtOAc/hexanes) to provide 4-(diphenylmethyleneamino)-5-fluoro-2,3-dihydro-1H-inden-2-ol (1.15 g, 3.47 mmol, 84%) which was used without further purification.

Workup

  1. filtrationfiltered through a layer of Celite
  2. washwashed with diethyl ether (60 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel chromatography (gradient elution: 0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b36db20c67e84047a43efecf51e58e26
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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