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Isobutylene oxide → 1-[5-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]-2-methylpropan-2-ol

HRID 385974
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HRID 385974 반응식
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[N:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.[O:14]1[C:16]([CH3:18])([CH3:17])[CH2:15]1.CC([O-])(C)C.[K+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]([CH2:15][C:16]([CH3:18])([OH:14])[CH3:17])[N:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 11208Isobutylene oxideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 1784328616-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine

생성물 1

HCID 595262551-[5-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]-2-methylpropan-2-ol

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

6-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine (131 mg, 0.68 mmol) and 1,2-epoxy-2-methylpropane (65 μl, 0.71 mmol) were taken-up in DMF (2.7 ml). Potassium 2-methylpropan-2-olate (114 mg, 1.01 mmol) was added, and the mixture was heated to 60° C. for seven hours. Saturated aqueous ammonium chloride was added and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated, purified by reverse-phase HPLC (10-100% acetonitrile/water with 0.05% trifluoroacetic acid modifier). The appropriate fractions were neutralized with aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.

후처리

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (10-100% acetonitrile/water with 0.05% trifluoroacetic acid modifier)
  6. extractionextracted twice with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8e16de72a4f94da390416b37e42a2ce7
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367706B2

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