Picolinic acid → 5-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amine

HRID 1622662노트

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HRID 1622662 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1C=CC=CC=1C(O)=O.[NH2:29][C:30]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)=[CH:34][C:33]([Cl:43])=[CH:32][N:31]=1.[NH4+].[Cl-]>CS(C)=O.[Cu]I>[Cl:43][C:33]1[CH:34]=[C:35]([C:36]2[CH:41]=[CH:40][C:39]([O:42][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=3)=[CH:38][CH:37]=2)[CH:30]([NH2:29])[NH:31][CH:32]=1

참가 물질

8

반응물 5

HCID 1018Picolinic acidHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenol

생성물 1

HCID 682809385-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amine수율 55.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

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온도
140 °C

실험 절차

A mixture of 4-bromo-2-(trifluoromethyl)pyridine (282 mg), tripotassium phosphate (481 mg), picolinic acid (27.9 mg), copper (I) iodide (21.58 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (250 mg) in DMSO (5 ml) was stirred at 140° C. under N2 overnight. The mixture was poured into sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (230 mg) as a pale yellow solid.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

출처 및 근거

ORD 기록
ord-067e0a9814b044838e012b7ac5b46074
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778934B2

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