Potassium Phosphate, Tribasic → HCID 89718115, compound

HRID 1518964Notes

Reaction equation

HRID 1518964 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>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].O1CCOCC1.O>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([C:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 112644642-(Benzyloxy)-6-chloropyridine

Product 1

HCID 89718115HCID 89718115, compoundYield 95.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

To a flask equipped with an N2 inlet adaptor, add 2-(benzyloxy)-6-chloropyridine (1.63 g, 7.42 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.3 g, 7.42 mmol), tris(dibenzylideneacetone)dipalladium(0) (339.5 mg, 371.0 μmol), potassium phosphate (3.94 g, 18.55 mmol), tricyclohexylphosphine (208 mg, 0.742 mmol), water (4 mL) and 1,4-dioxane (40 mL). Flush with N2, then heat the mixture at 95° C. overnight under a nitrogen atmosphere. Filter and concentrate under vacuum to give a residue. Purify via silica gel flash column chromatography using a gradient of 0-30% ethyl acetate in petroleum ether to give the title compound as a white solid (2.6 g, 95.6%). MS (m/z): 367 (M+1).

Workup

  1. customTo a flask equipped with an N2 inlet adaptor
  2. customFlush with N2
  3. filtrationFilter
  4. concentrationconcentrate under vacuum
  5. customto give a residue
  6. customPurify via silica gel flash column chromatography

Sources & evidence

ORD record
ord-94af5ce5da0345cfa1c3ced4b8064ce0
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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