Potassium Hydroxide → HCID 58168010, compound

HRID 1029277Notes

Reaction equation

HRID 1029277 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.Cl.Cl.[NH2:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([N:25]([CH3:27])[CH3:26])=[CH:23][CH:22]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(C)(C)C.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][N:25]([CH3:27])[C:24]1[CH:28]=[CH:29][C:21]([CH2:20][NH:19][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:22][CH:23]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168010HCID 58168010, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
170 °C

Procedure

6 (200 mg, 0.87 mmol), 4-(aminomethyl)-N,N-dimethylaniline dihydrochloride (774 mg, 3.47 mmol), Pd(OAc)2 (8 mg, 0.03 mmol), X-Phos (33 mg, 0.07 mmol), and KOH (438 mg, 8 mmol) were suspended in tert-butanol (3 mL), and stirred for 5 minutes at 170° C. via microwave. The reaction mixture was diluted with DMF and filtered. The crude product was purified directly via prep-LC-MS to provide 456 (6 mg, 2% yield) as a white powder. LC-MS (M+H=345, obsd.=345). 1H NMR (400 MHz, DMSO-D6) δ 11.46 (s, 1H), 8.58 (d, J=8.0, 1H), 8.42 (d, J=3.3, 1H), 7.97 (d, J=8.8, 2H), 7.38 (s, 1H), 7.26 (t, J=7.7, 2H), 7.08 (s, 1H), 6.71 (d, J=8.6, 2H), 4.35 (d, J=5.6, 2H), 2.85 (s, 6H).

Workup

  1. filtrationfiltered
  2. customThe crude product was purified directly via prep-LC-MS

Sources & evidence

ORD record
ord-0c6b3284b18e443eb39eb7050f4969ab
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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