Potassium Phosphate, Tribasic → HCID 70945481, compound

HRID 517998Notes

Reaction equation

HRID 517998 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:14]=1)[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].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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]>[NH2:32][C:33]1[C:38]([NH:39][CH3:40])=[CH:37][C:36]([C:16]2[CH:15]=[N:14][C:13]([O:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[C:18]([C:19]([F:20])([F:21])[F:22])[CH:17]=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 69932325HCID 69932325, compound

Product 1

HCID 70945481HCID 70945481, compoundYield 49%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A suspension of tert-butyl methyl(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)carbamate (440 mg), 3-amino-6-chloro-4-(methylamino)picolinonitrile (135 mg), tris(dibenzylideneacetone)dipalladium (0) (34.9 mg), tricyclohexylphosphine (25.7 mg) and potassium phosphate (327 mg) in 1,4-dioxane (10 ml) and water (5 ml) was stirred at 100° C. for 2 h. The reaction mixture was cooled and partitioned between water and ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. Purified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2) to give 170 mg orange amorphous as tert-butyl 2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl(methyl)carbamate (49%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2)

Sources & evidence

ORD record
ord-17b238368e8745368278ae3dc4d6fdcb
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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