Potassium Phosphate, Tribasic → HCID 89783385, compound

HRID 1056266Notes

Reaction equation

HRID 1056266 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC1(C)C(C)(C)OB([C:51]2[NH:59][C:58]3[CH2:57][CH2:56][NH:55][C:54](=[O:60])[C:53]=3[CH:52]=2)O1.Br[C:63]1[CH:64]=[CH:65][CH:66]=[C:67]2[C:72]=1[N:71]=[C:70]([C:73]1[C:78]([CH3:79])=[CH:77][CH:76]=[CH:75][C:74]=1[CH3:80])[CH:69]=[N:68]2>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:80][C:74]1[CH:75]=[CH:76][CH:77]=[C:78]([CH3:79])[C:73]=1[C:70]1[CH:69]=[N:68][C:67]2[C:72]([N:71]=1)=[C:63]([C:51]1[NH:59][C:58]3[CH2:57][CH2:56][NH:55][C:54](=[O:60])[C:53]=3[CH:52]=1)[CH:64]=[CH:65][CH:66]=2

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 89782036HCID 89782036, compoundHCID 897834962-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-one

Product 1

HCID 89783385HCID 89783385, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Argon was bubbled into a mixture of potassium phosphate tribasic (0.28 g, 1.02 mmol), Xphos (Strem, 0.012 g, 0.026 mmol), Pd2dba3 (Strem; 0.012 g, 0.013 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (0.201 g, 0.766 mmol), 8-bromo-2-(2,6-dimethylphenyl)quinoxaline (401a; 0.08 g, 0.255 mmol) in 2 mL dioxane and 0.4 mL water for 2 min. The reaction was sealed and heated to 80° C. After 3 h, the reaction was cooled and 1.6 g silica gel was added, and the material dried in vacuo. The material was purified by silica gel chromatography (24 g ISCO gold column) using 0-50% 90/10 DCM/MeOH in DCM. The product-containing fractions were concentrated to afford 2-(3-(2,6-dimethylphenyl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.055 g, 0.149 mmol, 58% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.77 (1H, br. s.), 8.97 (1H, s), 8.14 (1H, dd, J=7.3, 1.3 Hz), 7.95-8.02 (1H, m), 7.86-7.94 (1H, m), 7.31-7.39 (1H, m), 7.21-7.31 (3H, m), 6.98 (1H, s), 3.40 (2H, td, J=6.8, 2.3 Hz), 2.85 (2H, t, J=6.8 Hz), 2.10 (6H, s). m/z (ESI, +ve) 369.0 (M+H)+.

Workup

  1. customThe reaction was sealed
  2. temperaturethe reaction was cooled
  3. addition1.6 g silica gel was added
  4. customthe material dried in vacuo
  5. customThe material was purified by silica gel chromatography (24 g ISCO gold column)
  6. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-3f514437ce0d4380bfc52c0a560d3b37
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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