2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 58168249, compound

HRID 1029175Notes

Reaction equation

HRID 1029175 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]2[O:26][CH2:27][O:28][C:24]=2[C:23]=1[NH2:31].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]2[O:26][CH2:27][O:28][C:24]=2[C:23]=1[NH:31][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2

Participants

8

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 23676156Sodium t-butoxideHCID 58168153HCID 58168153, compound

Product 1

HCID 58168249HCID 58168249, compoundYield 3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Compound 211 (50 mg, 0.17 mmol), 5-chloro-benzo[1,3]dioxol-4-ylamine (38 mg, 0.22 mmol), Pd(OAc)2 (2 mg, 0.01 mmol), X-Phos (8 mg, 0.02 mmol), and NaOtBu (50 mg, 0.52 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O, and filtered. The resulting precipitate was washed with EtOAc/H2O, and then suspended in methanolic HCl. The crude product was purified via prep-LC-MS to provide 212 (2 mg, 3% yield) as a white solid. LC-MS (M+H=426, obsd.=426).

Workup

  1. filtrationfiltered
  2. washThe resulting precipitate was washed with EtOAc/H2O
  3. customThe crude product was purified via prep-LC-MS

Sources & evidence

ORD record
ord-a27ffa9f29664e658b7ff1d995d0a00c
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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