Cesium carbonate → HCID 86720999, compound

HRID 524941Notes

Reaction equation

HRID 524941 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.I[C:44]1[C:45]([O:59][CH3:60])=[CH:46][C:47]([N:50]([CH3:58])[C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[N:48][CH:49]=1.[C:61]1([C:67]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[NH:68])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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:61]1([C:67](=[N:68][C:44]2[C:45]([O:59][CH3:60])=[CH:46][C:47]([N:50]([CH3:58])[C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[N:48][CH:49]=2)[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58053580HCID 58053580, compound

Product 1

HCID 86720999HCID 86720999, compoundYield 69.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Pd2(dba)3 (33.70 mg, 0.03680 mmol) and Xantphos (42.58 mg, 0.07359 mmol) were added to a sealed tube containing tert-butyl N-(5-iodo-4-methoxy-2-pyridyl)-N-methyl-carbamate (268 mg, 0.7359 mmol), diphenylmethanimine (173.4 mg, 160.6 μL, 0.9567 mmol) and Cs2CO3 (719.4 mg, 2.208 mmol) in dioxane (2.5 mL). The reaction was placed under an atmosphere of nitrogen and heated at 100° C. for 4 hours. At RT, the reaction mixture was filtered through celite and the filtrate concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 30% EtOAc/Petroleum Ether, loaded in DCM) to give tert-butyl (5-((diphenylmethylene)amino)-4-methoxypyridin-2-yl)(methyl)carbamate as a yellow solid (213 mg, 69% Yield). MS (ES+) 418.2.

Workup

  1. filtrationAt RT, the reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 30% EtOAc/Petroleum Ether, loaded in DCM)

Sources & evidence

ORD record
ord-850e54f3b4204319adf7693692a72315
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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