Potassium Phosphate, Tribasic → HCID 67294207, compound

HRID 518004Notes

Reaction equation

HRID 518004 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:11]([C:26]([F:29])([F:28])[F:27])[CH:10]=2)O1.[NH2:31][C:32]1[C:33]([C:41]#[N:42])=[N:34][C:35](Cl)=[CH:36][C:37]=1[NH:38][CH3:39].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C(OCC)(=O)C.O>[NH2:31][C:32]1[C:37]([NH:38][CH3:39])=[CH:36][C:35]([C:9]2[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[C:11]([C:26]([F:27])([F:28])[F:29])[CH:10]=2)=[N:34][C:33]=1[C:41]#[N:42]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 67294284HCID 67294284, compound

Product 1

HCID 67294207HCID 67294207, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-phenoxy)ethylcarbamate (4.34 mmol, 1.87 g), 3-amino-6-chloro-4-(methylamino)-picolinonitrile (4.34 mmol, 0.792 g), potassium phosphate (13.01 mmol, 2.76 g), tricyclohexylphosphine (0.520 mmol, 0.146 g), and tris(dibenzylacetone)dipalladium (0) (0.217 mmol, 0.199 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)ethylcarbamate. (0.51 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-6ebc81b2d39b4f3f8086a96a33a2d851
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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