Dichloromethane → HCID 57938632, compound

HRID 1435844Notes

Reaction equation

HRID 1435844 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].ClCCl.C(=O)([O-])[O-].[K+].[K+].[C:53]([O:57][C:58](=[O:69])[NH:59][CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65](Br)=[CH:64][CH:63]=1)([CH3:56])([CH3:55])[CH3:54]>O1CCOCC1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:53]([O:57][C:58](=[O:69])[NH:59][CH2:60][CH2:61][C:62]1[CH:63]=[CH:64][C:65]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:66][CH:67]=1)([CH3:56])([CH3:54])[CH3:55]

Participants

10

Reactant 6

HCID 6344Dichloromethane2×HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonateHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 57938632HCID 57938632, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalyst2×HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1,1,1-trifluoromethanesulfonic acid 6-methoxy[1,5]naphthyridin-4-yl ester (1.0 g, 3.24 mmole) in dry dioxane (50 mL) at RT was added bis(pinacolato)diboron (1.07 g, 4.22 mmole), potassium acetate (0.95 g, 9.72 mmole), 1,1-bis(diphenylphosphino)ferrocene (0.09 g, 0.16 mmole) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.13 g, 0.16 mmole). The reaction contents were heated to 80° C. for 24 h under nitrogen gas and then 1, 1-bis(diphenylphosphino)ferrocene (0.09 g, 0.16 mmole), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.13 g, 0.16 mmole), potassium carbonate (1.34 g, 9.72 mmole) and [2-(4-bromophenyl)ethyl]carbamic acid tert-butyl ester (0.97 g, 3.24 mmole) were added to the reaction pot. After 24 h of vigorous stirring at 80° C., the reaction contents were filtered through a scinter-glass funnel containing a bed of celite (EtOAc). The filtrate was concentrated under vacuum and purified on silica (EtOAc) to afford the title compound (0.76 g, 62%) as a tan solid: LC-MS (ES) m/e 380 (M+H)+.

Workup

  1. customThe reaction contents
  2. additionwere added to the reaction pot
  3. customthe reaction contents
  4. filtrationwere filtered through a scinter-glass funnel
  5. additioncontaining a bed of celite (EtOAc)
  6. concentrationThe filtrate was concentrated under vacuum
  7. custompurified on silica (EtOAc)

Sources & evidence

ORD record
ord-078c1dff49b64af7895598f77119fa38
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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