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

HRID 517992
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HRID 517992 반응식
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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-eafc768ed4b84598a689eaad68ecc163
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115126B2

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