(4-Methoxyphenyl)boronic acid → HCID 58167946, compound

HRID 1029073Notes

Reaction equation

HRID 1029073 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7](=[O:15])[C:6]=2[CH:16]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:12]2[CH:13]=[C:14]3[C:9](=[N:10][CH:11]=2)[NH:8][C:7](=[O:15])[C:6]2[CH:16]=[CH:2][CH:3]=[CH:4][C:5]3=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 201262(4-Methoxyphenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 58168076HCID 58168076, compound

Product 1

HCID 58167946HCID 58167946, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

8-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-methoxyphenylboronic acid (66 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (9 mg, 0.02 mmol), and sodium tert-butoxide (63 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 diluted with MeOH, filtered through a membrane plug, and purified via prep-LC-MS to provide 14 (10 mg, 15% yield) as a white solid. LC-MS (M+H=303, obsd.=303). 1H NMR (400 MHz, d6-DMSO): δ 12.11 (s, 1H), 8.84 (d, 1H), 8.61 (d, 1H), 8.52 (dd, 1H), 8.18 (dd, 1H), 7.80 (d, 2H), 7.34 (dd, 1H), 7.10 (d, 2H), 6.93 (s, 1H), 3.83 (s, 3H).

Workup

  1. filtrationfiltered through a membrane plug
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-5f05b694b475446ea44eb36d473105f4
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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