Benzophenone imine → HCID 22607380, compound

HRID 2307764Notes

Reaction equation

HRID 2307764 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:11]=[CH:12][N:13]=[CH:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH:5]=[N:6][CH:7]=1.[C:19](=[NH:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>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]>[C:26]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:32][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([NH:8][C:9]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:10]=3[CH:11]=[CH:12][N:13]=[CH:14]4)[CH:3]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 22607689HCID 22607689, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 22607380HCID 22607380, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 23C (175 mg, 0.58 mmol), benzophenone imine (150 mg, 0.83 mmol), Pd2(dba)3 (54 mg, 0.06 mmol), BINAP (55 mg, 0.09 mmol), and sodium tert-butoxide (80 mg, 0.82 mmol) in 3 mL toluene was heated to 75-80° C. for 4 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane to provide the desired product (150 mg, 64%).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-62ac61125dc140ad8562f49bb64ceec7
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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