Benzophenone imine → HCID 90093186, compound

HRID 1753059Notes

Reaction equation

HRID 1753059 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][N:27]=1)[C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.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:2]1([C:1](=[N:14][C:16]2[CH:17]=[C:18]([CH:25]=[CH:26][N:27]=2)[C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 448186542-Bromo-N-methoxy-N-methylisonicotinamide

Product 1

HCID 90093186HCID 90093186, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Benzophenone imine (2.17 g, 12.0 mmol) was added to 2-bromo-N-methoxy-N-methylisonicotinamide (2.45 g, 10.0 mmol), tris(dibenzylideneacetone)dipalladium (458 mg, 0.50 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (552 mg, 1.30 mmol) and sodium t-butoxide (2.40 g, 25.0 mmol) in toluene (40 mL). The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with DCM and filtered through Arbocel™. The filtrate was washed with water (100 mL) then the organic phase was dried over sodium sulphate and evaporated in vacua. The crude material was purified by silica gel column chromatography eluting with heptane:EtOAc 100:0 to 30:70 to afford the title compound as an orange gum (71%, 2.44 g).

Workup

  1. filtrationfiltered through Arbocel™
  2. washThe filtrate was washed with water (100 mL)
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customevaporated in vacua
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with heptane:EtOAc 100:0 to 30:70

Sources & evidence

ORD record
ord-8bbb6d6479744e3abc0d2e69c0e04785
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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