Potassium Phosphate, Tribasic → HCID 67294345, compound

HRID 518008Notes

Reaction equation

HRID 518008 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][C:14]=1[C:28]([F:31])([F:30])[F:29])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[NH2:32][C:33]1[C:34]([C:42]#[N:43])=[N:35][C:36](Cl)=[CH:37][C:38]=1[NH:39][CH3:40].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C(OCC)(=O)C.O>[NH2:32][C:33]1[C:38]([NH:39][CH3:40])=[CH:37][C:36]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:8])[CH3:7])=[C:14]([C:28]([F:29])([F:30])[F:31])[CH:15]=2)=[N:35][C:34]=1[C:42]#[N:43]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 67294078HCID 67294078, compound

Product 1

HCID 67294345HCID 67294345, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)ethyl)carbamate (22.46 mmol, 10 g), 3-amino-6-chloro-4-(methylamino)picolinonitrile (22.46 mmol, 4.10 g), potassium phosphate (67.4 mmol, 14.30 g), tricyclohexylphosphine (2.69 mmol, 0.756 g), and tris(dibenzylacetone)-dipalladium (0) (1.123 mmol, 1.028 g) were dissolved in Dioxane (20 ml) and Water (10.00 ml) and stirred under nitrogen at 100° C. for 2 hrs. The mixture was diluted with ethyl acetate and filtered through celite. Organic layer was washed with water and separated from the aqueous layer, the organic layer was concentrated in vacuo. This was purified by silica chromatography, eluting with heptane—50/50 heptane/EtOAc to afford tert-butyl 2-(4-(5-amino-6-cyano-4-(methylamino)pyridin-2-yl)-2-(trifluoro-methyl)phenoxy)ethyl(methyl)carbamate. (2.11 g)

Workup

  1. filtrationfiltered through celite
  2. washOrganic layer was washed with water
  3. customseparated from the aqueous layer
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThis was purified by silica chromatography
  6. washeluting with heptane—50/50 heptane/EtOAc

Sources & evidence

ORD record
ord-044342ad0ed74bf69337aa467b0c5228
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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