Cesium carbonate → HCID 58168328, compound

HRID 1029129Notes

Reaction equation

HRID 1029129 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+].[C:57]([C:59]1[CH:64]=[CH:63][CH:62]=[C:61]([O:65][CH3:66])[CH:60]=1)#[CH:58]>O1CCOCC1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:66][O:65][C:61]1[CH:60]=[C:59]([C:57]#[C:58][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)[CH:64]=[CH:63][CH:62]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6407531-Ethynyl-3-methoxybenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168328HCID 58168328, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

Compound 83 (100 mg, 0.43 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and Cs2CO3 (424 mg, 1.30 mmol) were suspended in dioxane (2 mL), and stirred for 20 minutes at room temperature. 1-Ethynyl-3-methoxy-benzene (86 mg, 0.65 mmol) was then added, and the resulting solution was stirred for 3 h at 100° C. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 160 (80 mg, 56% yield) as a light-yellow solid. LC-MS (M+H=327, obsd.=327).

Workup

  1. stirringthe resulting solution was stirred for 3 h at 100° C
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with EtOAc/H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cd225eedc7894737ad9098c37794d4c8
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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