3-Methoxyaniline → HCID 58168307, compound

HRID 1029194Notes

Reaction equation

HRID 1029194 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+].[CH3:57][O:58][C:59]1[CH:64]=[CH:63][CH:62]=[C:61]([NH2:65])[CH:60]=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:57][O:58][C:59]1[CH:60]=[C:61]([NH:65][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)[CH:62]=[CH:63][CH:64]=1

Participants

7

Reactant 4

HCID 108243-MethoxyanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168307HCID 58168307, compoundYield 20.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Compound 6 (50 mg, 0.22 mmol), Pd(OAc)2 (4 mg, 0.02 mmol), X-Phos (17 mg, 0.03 mmol), NaOtBu (125 mg, 1.30 mmol), and m-anisidine (0.04 mL, 0.33 mmol) were dissolved in dioxane (2 ml) and stirred for 72 hrs at 100° C. The crude material was purified directly via Biotage eluting with a gradient of 0 to 10% MeOH in CH2Cl2 to provide 231 (14 mg, 19% yield) as a white solid. LC-MS (M+H=318, obsd.=318).

Workup

  1. customThe crude material was purified directly via Biotage
  2. washeluting with a gradient of 0 to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-d9cdaed93f0049ba880c5e5af872bd29
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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