Potassium Phosphate, Tribasic → HCID 56646860, compound

HRID 2365243Notes

Reaction equation

HRID 2365243 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]3[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=3[C:12]3[CH2:13][N:14]([C@H:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]4[OH:25])[C:15](=[O:18])[C:16]=3[CH:17]=2)=[CH:4][CH:3]=1.[CH:30]([B-](F)(F)F)=[CH2:31].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C(=O)(O)[O-].[Na+].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]>[OH:25][C@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:19]1[N:14]1[CH2:13][C:12]2[C:11]3[CH:26]=[CH:27][CH:28]=[CH:29][C:10]=3[C:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([CH:30]=[CH2:31])=[CH:3][CH:4]=3)=[CH:17][C:16]=2[C:15]1=[O:18]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 23679353Potassium vinyltrifluoroborateHCID 86682401HCID 86682401, compound

Product 1

HCID 56646860HCID 56646860, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-[(6-chloropyridin-3-yl)methyl]-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.050 g, 0.12 mmol) in 1 mL of dioxane was added potassium vinyltrifluoroborate (0.033 g, 0.25 mmol), aqueous potassium phosphate (1.27 M, 0.16 mL, 0.21 mmol), tricyclohexylphosphine (0.83 mg, 0.0030 mmol), and tris[dibenzylideneacetone]dipalladium (0) (1.2 mg, 0.0012 mmol). The mixture was irradiated in a microwave reactor at 140° C. for 30 min, cooled to ambient temperature, and diluted with saturated aqueous sodium bicarbonate. The mixture was extracted twice with dichloromethane and the combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 399.2 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1H), 7.99-7.97 (m, 1H), 7.89-7.87 (m, 1H), 7.68 (s, 1H), 7.61-7.54 (m, 2H), 7.33-7.30 (m, 1H), 7.18-7.16 (m, 1H), 6.79-6.72 (m, 1H), 5.44-5.30 (m, 1H), 4.85-4.70 (m, 2H), 4.39 (s, 2H), 4.21-4.14 (m, 1H), 3.80-3.75 (m, 1H), 2.63-2.61 (m, 1H), 2.24-2.20 (m, 1H), 2.02-1.85 (m, 2H), 1.72-1.68 (m, 1H), 1.62-1.41 (m, 3H) ppm.

Workup

  1. customThe mixture was irradiated in a microwave reactor at 140° C. for 30 min
  2. extractionThe mixture was extracted twice with dichloromethane
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-9c934652c44f4ce59c55826138a5ae53
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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