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Water → 3-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile

HRID 517992
Notes
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Reaction equation

HRID 517992 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=2)O1.[NH2:24][C:25]1[C:26]([C:34]#[N:35])=[N:27][C:28](Cl)=[CH:29][C:30]=1[NH:31][CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C.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]>[NH2:24][C:25]1[C:26]([C:34]#[N:35])=[N:27][C:28]([C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:10]=2)=[CH:29][C:30]=1[NH:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 672940732-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)ethanol

Product 1

HCID 709451293-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile
Yield 146.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)ethanol (7.1 g), 3-amino-6-chloro-4-(methylamino)picolinonitrile (21.38 mmol, 3.90 g), potassium phosphate, tribasic (13.61 g), tricyclohexylphosohine (0.719 g), and tris(dibenzylideneacetone)dipalladium(0) (0.979 g) were dissolved in Dioxane (100 ml) and Water (40.0 ml) and stirred under nitrogen at 100° C. for 3 hrs. The mixture was diluted with ethyl acetate and filtered through celite. Filtrate was washed with water (300 ml), organic layer extracted and concentrated in vacuo to give crude 3-amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile (11 g). 1H NMR (MeOH) δ: 8.07 (s, 1H), 8.00 (d, 1H), 7.70 (m, 1H), 7.42 (m, 1H), 7.25 (m, 1H), 4.20 (t, 2.5), 3.93 (t, 2.5), 3.66 (s, 1.5), 2.98 (s, 3.5). MS m/z 353 (M+H).

Workup

  1. filtrationfiltered through celite
  2. washFiltrate was washed with water (300 ml), organic layer
  3. extractionextracted
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eafc768ed4b84598a689eaad68ecc163
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115126B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes