Benzophenone imine → HCID 118378989, compound

HRID 931022Notes

Reaction equation

HRID 931022 reaction equation
[C@H:1]12[CH2:23][C@H:4]([N:5]([C:7]([C:9]3[N:13]4[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:17](Br)[C:12]4=[N:11][CH:10]=3)=[O:8])[CH2:6]1)[CH2:3][O:2]2.C1(C(C2C=CC=CC=2)=[NH:31])C=CC=CC=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.[Cl-].[NH4+].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]>[NH2:31][C:17]1[C:12]2[N:13]([C:9]([C:7]([N:5]3[CH2:6][C@@H:1]4[CH2:23][C@H:4]3[CH2:3][O:2]4)=[O:8])=[CH:10][N:11]=2)[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 118378882HCID 118378882, compound

Product 1

HCID 118378989HCID 118378989, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 25517Ammonium ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl(8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone (300 mg), 1,1-diphenylmethanimine (209 mg), tris(dibenzylideneacetone)dipalladium(0) (17.6 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (44.5 mg) and sodium tert-butoxide (111 mg) in 1,4-dioxane (4.0 mL) was stirred with microwave irradiation at 120° C. for 60 min. The reaction mixture was diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was diluted with THF, 1N hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (207 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was diluted with THF, 1N hydrochloric acid
  6. additionwas added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. additionThe reaction mixture was diluted with aqueous sodium hydrogen carbonate solution
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water and saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d218e58eec6247318282108d8fb3c3fd
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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