Potassium Hydroxide → HCID 58168126, compound

HRID 1029128Notes

Reaction equation

HRID 1029128 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.[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26]C(NC2CCNCC2)=O)=[CH:22][CH:21]=1)([CH3:19])[CH3:18].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(CC)(C)C.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][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:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-oneHCID 68648690HCID 68648690, compound

Product 1

HCID 58168126HCID 58168126, compoundYield 28.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 64052-Methyl-2-butanolSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Compound 83 (100 mg, 0.43 mmol), 1-(4-isopropyl-phenyl)-3-piperidin-4-yl-urea (136 mg, 0.52 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and KOH (73 mg, 1.30 mmol) were suspended in tert-amyl alcohol (2 mL), and stirred overnight 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 159 (40 mg, 28% yield) as a tan solid. LC-MS (M+H=330, obsd.=330).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc/H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bbf04dd138ef41cb87a0357aa2ad6e27
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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