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

HRID 594256ノート

反応式

HRID 594256 の反応式
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

参加物

8

反応物 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 16217886Methyl 6-bromopyridine-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2d6d409504ff4c8c81c486c7af79c570
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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