Dimethylformamide → 5-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile

HRID 517678

반응식

HRID 517678 반응식
Br[C:2]1[C:7]([N:8]2[N:12]=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:5]=[C:4](C)[N:3]=1.[C:14]([O-])([O-])=O.[K+].[K+].[N:20]1N[N:22]=[CH:23][CH:24]=1.[CH3:25][N:26](C=O)C>>[CH3:25][C:5]1[CH:6]=[C:7]([N:8]2[N:9]=[CH:10][CH:11]=[N:12]2)[C:2]([C:24]#[N:20])=[N:3][CH:4]=1.[CH3:14][C:5]1[CH:6]=[C:7]([N:8]2[CH:24]=[CH:23][N:22]=[N:12]2)[C:2]([C:25]#[N:26])=[N:3][CH:4]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 675161H-1,2,3-TriazoleHCID 90404199HCID 90404199, 화합물

생성물 2

HCID 904052945-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile수율 27%HCID 904059695-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile수율 35%

반응 조건

온도
100 °C

실험 절차

To 2-bromo-6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridine (1.5 g, 7.6 mmol) in DMF (19 mL) was added K2CO3 (1.2 g, 8.4 mmol) and 2H-1,2,3-triazole (440 μL, 7.6 mmol). The mixture was heated to 100° C. for 16 h, cooled to rt and extracted with EtOAc (2×). The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (5-60% EtOAc in hexanes) gave the title compound (490 mg, 35%) and 5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile (387 mg, 27%).

후처리

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography (5-60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-29dd7edd4ae446d6a6fd40fa78731d2d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115117B2

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