Potassium Carbonate → HCID 58168004, compound

HRID 1029122Notes

Reaction equation

HRID 1029122 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.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.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]>[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[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

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168004HCID 58168004, compoundYield 10%

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), 2-fluorophenylboronic acid (46 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, diluted with MeOH/DMSO, and filtered. The filtrate was purified via prep-LC-MS. The product was triturated with MeOH, filtered, and dried under vacuum to provide 153 (6 mg, 10% yield) as a white solid. LC-MS (M+H=291, obsd.=291).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with MeOH/DMSO
  3. filtrationfiltered
  4. customThe filtrate was purified via prep-LC-MS
  5. customThe product was triturated with MeOH
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-77f10048c6534417a443da4fc2fc3fad
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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