Pyrazole → 4-Pyridinecarboxylic acid, 2-(1H-pyrazol-1-yl)-, methyl ester

HRID 594253노트

반응식

HRID 594253 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I.O>[N:12]1([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:16]=[CH:15][CH:14]=[N:13]1

참가 물질

8

반응물 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 38477682-Bromo-isonicotinic acid methyl ester

생성물 1

HCID 690832694-Pyridinecarboxylic acid, 2-(1H-pyrazol-1-yl)-, methyl ester

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of commercially available methyl 2-bromoisonicotinate (500 mg; 2.31 mmol), 1H-pyrazole (157 mg; 2.31 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (67 mg; 0.46 mmol), K2CO3 (685 mg; 4.86 mmol), and CuI (22 mg; 0.11 mmol) in anh. toluene (8 ml) was heated at reflux for 16 h. After cooling to rt, water was added, and the mixture was extracted with AcOEt. The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded methyl 2-(1H-pyrazol-1-yl)isonicotinate as an off-white solid. LC-MS (conditions A): tR=0.67 min.; [M+H]+: 204.04 g/mol.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionthe mixture was extracted with AcOEt
  4. dry with materialThe mixed organic layers were dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=20/1)

출처 및 근거

ORD 기록
ord-fe7b9d883a184bb49983791d1120547f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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