Potassium Carbonate → HCID 58168268, compound

HRID 1029121Notes

Reaction equation

HRID 1029121 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.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([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][CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168268HCID 58168268, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

Compound 83 (50 mg, 0.22 mmol), 3-methoxyphenylboronic acid (49 mg, 0.33 mmol), Pd(OAc)2 (2 mg, 0.01 mmol), S-Phos (9 mg, 0.02 mmol), and K2CO3 (90 mg, 0.65 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated. The crude product was purified directly via Biotage eluting with a gradient of 25 to 85% EtOAc in hexanes to provide 152 (11 mg, 17% yield) as a white solid. LC-MS (M+H=303, obsd.=303).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified directly via Biotage
  3. washeluting with a gradient of 25 to 85% EtOAc in hexanes

Sources & evidence

ORD record
ord-bf9900f0294440a1979c4245326611fd
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…