Pyrazole → methyl 6-(1H-pyrazol-1-yl)picolinate

HRID 594256노트

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HRID 594256 반응식
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.[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[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=2)[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 16217886Methyl 6-bromopyridine-2-carboxylate

생성물 1

HCID 69083337methyl 6-(1H-pyrazol-1-yl)picolinate

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 6-bromopicolinate (1.000 g; 4.62 mmol), 1H-pyrazole (315 mg; 4.62 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (135 mg; 0.92 mmol), K2CO3 (1.370 g; 9.72 mmol), and CuI (44 mg; 0.23 mmol) in anh. toluene (15 ml) was heated at reflux for 17 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 6-(1H-pyrazol-1-yl)picolinate as a colorless solid. LC-MS (conditions A): tR=0.59 min.; [M+H]+: 204.04 g/mol.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 17 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-2d6d409504ff4c8c81c486c7af79c570
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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