Picolinic acid → 3-(4-(3-Methoxyphenoxy)phenyl)pyridin-2-amine

HRID 1622680

반응식

HRID 1622680 반응식
N1C=CC=CC=1C(O)=O.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=1>[Cu]I.CS(C)=O>[CH3:40][O:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[C:11]([NH2:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 69839Benzene, 1-iodo-3-methoxy-HCID 667484774-(2-Aminopyridin-3-yl)phenol

생성물 1

HCID 667488603-(4-(3-Methoxyphenoxy)phenyl)pyridin-2-amine수율 44.5%

시약·촉매·용매 2

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

반응 조건

온도
120 °C

실험 절차

Copper(I) iodide (102 mg) was added to a mixture of picolinic acid (66.1 mg), 4-(2-aminopyridin-3-yl)phenol (500 mg), tripotassium phosphate (1710 mg), 1-iodo-3-methoxybenzene (754 mg) and DMSO (8 mL). The mixture was stirred at 120° C. under nitrogen for 6 hr. The insoluble material was removed by silica-filtration with EtOAc, and the filtrate was extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous sodium 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 (349 mg) as a yellow solid.

후처리

  1. customThe insoluble material was removed by silica-filtration with EtOAc
  2. extractionthe filtrate was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

출처 및 근거

ORD 기록
ord-0fbfcca41073476da3c6155aa99e747d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778934B2

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