Aniline → HCID 58168332, compound

HRID 1029072Notes

Reaction equation

HRID 1029072 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.N[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C[C:59](C)([O-:61])C.[Na+].[O:64]1CCOC[CH2:65]1>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:65][O:64][C:59](=[O:61])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[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

Participants

8

Reactant 5

HCID 6115AnilineHCID 312751,4-DioxaneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 58167982HCID 58167982, compound

Product 1

HCID 58168332HCID 58168332, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), aniline (40 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (10 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), 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 11 (39 mg, 63% yield) as a white solid. LC-MS (M+H=288, obsd.=288). 1H NMR (400 MHz, d6-DMSO): δ 11.94 (s, 1H), 8.45 (d, 1H), 8.41 (d, 1H), 8.32 (m, 2H), 7.87 (dt, 1H), 7.69 (dt, 1H), 7.27 (dd, 2H), 7.09 (dd, 2H), 6.82 (t, 1H).

Workup

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

Sources & evidence

ORD record
ord-bae3d5b607ff4c28af7455a5578aa4ea
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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