Benzophenone imine → HCID 86647084, compound

HRID 1812413Notes

Reaction equation

HRID 1812413 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:9]([S:16]([CH:19]2[CH2:21][CH2:20]2)(=[O:18])=[O:17])S(C2CC2)(=O)=O)[C:5]([Cl:8])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[C:70](=[NH:83])([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=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].CN(C=O)C>[Cl:8][C:5]1[C:4]([NH:9][S:16]([CH:19]2[CH2:20][CH2:21]2)(=[O:17])=[O:18])=[CH:3][C:2]([N:83]=[C:70]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 86647085HCID 86647085, compound

Product 1

HCID 86647084HCID 86647084, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a 20 mL microwave vial was added N-(5-bromo-2-chloropyridin-3-yl)-N-(cyclopropylsulfonyl)cyclopropanesulfonamide (0.880 g, 2.117 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Acros) (0.122 g, 0.212 mmol), tris(dibenzylideneacetone)dipalladium (0) (Strem) (0.097 g, 0.106 mmol), sodium tert-butoxide (Fluka) (0.814 g, 8.47 mmol), DMF (10 mL), and benzophenone imine (Aldrich) (0.426 mL, 2.54 mmol). The resulting mixture was degassed by bubbling N2 for 5 min. It was sealed off and microwave heated at 130° C. for 20 min. The resulting mixture was partitioned between EtOAc and sat. NH4Cl (25 mL). The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (80 g, 10% to 20% acetone in hexanes) to afford the desired product as a yellow foam-like solid (300 mg). MS (ESI pos. ion) m/z: 412.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.89 (d, J=7.02 Hz, 2H) 1.03 (d, J=3.07 Hz, 2H) 6.60 (br. s., 1H) 7.14 (d, J=3.65 Hz, 2H) 7.34 (d, J=6.28 Hz, 4H) 7.39-7.48 (m, 2H) 7.49-7.56 (m, 1H) 7.68-7.80 (m, 3H).

Workup

  1. customThe resulting mixture was degassed
  2. customby bubbling N2 for 5 min
  3. customIt was sealed off
  4. customThe resulting mixture was partitioned between EtOAc and sat. NH4Cl (25 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (80 g, 10% to 20% acetone in hexanes)

Sources & evidence

ORD record
ord-690805a68f8e40efbf641d7fad00882e
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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