2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 58168170, compound

HRID 1029127Notes

Reaction equation

HRID 1029127 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.[NH2:17][C:18]1[C:19]([F:30])=[CH:20][C:21]([F:29])=[C:22]([CH:28]=1)[C:23]([NH:25][O:26][CH3:27])=[O:24].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]>[F:29][C:21]1[CH:20]=[C:19]([F:30])[C:18]([NH:17][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:28][C:22]=1[C:23]([NH:25][O:26][CH3:27])=[O:24]

Participants

8

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11264133HCID 11264133, compoundHCID 23676156Sodium t-butoxideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168170HCID 58168170, compoundYield 3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Compound 83 (100 mg, 0.43 mmol), 5-amino-2,4-difluoro-N-methoxy-benzamide (124 mg, 0.52 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and NaOtBu (125 mg, 1.30 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 10% MeOH in DCM to provide 158 (5 mg, 3% yield) as a white solid. LC-MS (M+H=397, obsd.=397).

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via Biotage
  5. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-37deb584bcd64f4f8616ae47101685d8
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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