Potassium Phosphate, Tribasic → HCID 59216381, compound

HRID 2245741Notes

Reaction equation

HRID 2245741 reaction equation
[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6](Br)[CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:45][N:46]([CH3:78])[C:47]1[CH:48]=[C:49]2[C:54](=[CH:55][CH:56]=1)[C:53](=[O:57])[N:52]([C:58]1[CH:68]=[CH:67][CH:66]=[C:65](B3OC(C)(C)C(C)(C)O3)[C:59]=1[CH2:60][O:61][C:62](=[O:64])[CH3:63])[CH2:51][CH2:50]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OC(=O)C)C.O.C(O)CCC>[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([C:65]2[CH:66]=[CH:67][CH:68]=[C:58]([N:52]3[CH2:51][CH2:50][C:49]4[C:54](=[CH:55][CH:56]=[C:47]([N:46]([CH3:78])[CH3:45])[CH:48]=4)[C:53]3=[O:57])[C:59]=2[CH2:60][O:61][C:62](=[O:64])[CH3:63])[CH:7]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-oneHCID 59216471HCID 59216471, compound

Product 1

HCID 59216381HCID 59216381, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

3-Amino-5-bromo-1-methyl-1H-pyridin-2-one (392 mg, 1.93 mmol) was placed into 13 ml n-butanol. To this mixture under argon was added: Pddba2 (55.2 mg, 0.096 mmol), XPhos (91.2 mg, 0.191 mmol), acetic acid 2-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (900 mg, 1.93 mmol), potassium phosphate (814 mg, 3.84 mmol) and 4 ml water. The mixture was heated under argon in a sealed flask for 45 minutes at 100-110° C. After cooling, the mixture was diluted with ethylacetate, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromathography using 5% methanol in dichloromethylene to afford 450 mg of Acetic acid 2-(5-amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester (49% yield).

Workup

  1. additionTo this mixture under argon was added
  2. temperatureAfter cooling
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromathography

Sources & evidence

ORD record
ord-674397664c9945b6a97079b9a7eb718f
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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