P-Anisidine → HCID 58167987, compound

HRID 1029102Notes

Reaction equation

HRID 1029102 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]1[CH:13]=[CH:14][CH:15]=[CH:16][C:5]2=1.CO[C:19]1[CH:25]=[CH:24][C:22](N)=[CH:21][CH:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C[C:61](C)([O-:63])C.[Na+]>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:61]([O:63][C:15]1[CH:14]=[CH:13][C:6]2[C:7](=[O:12])[NH:8][C:9]3[C:4]([C:5]=2[CH:16]=1)=[CH:3][CH:2]=[CH:11][N:10]=3)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 7732P-AnisidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 58167982HCID 58167982, compound

Product 1

HCID 58167987HCID 58167987, compoundYield 38.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 4-methoxy aniline (32 mg, 0.26 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (6 mg, 0.02 mmol), and sodium tert-butoxide (38 mg, 0.39 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 87 (15 mg, 36% yield) as a solid. LC-MS (M+H=318, obsd.=318). 1H NMR (400 MHz, d6-DMSO): δ 11.86 (s, 1H), 8.33 (dd, 2H), 8.22 (m, 2H), 7.88 (dt, 1H), 7.68 (m, 1H), 7.11 (d, 2H), 6.91 (d, 2H), 3.73 (s, 3H).

Workup

  1. filtrationfiltered
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-f1b0a8df602b43bc810a3235136a8f29
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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