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Sodium hydride → 3-Chloro-6-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridazine

HRID 402447
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HRID 402447 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH2:15][OH:16])=[C:13]([CH3:17])[N:12]=[N:11]2)=[CH:6][CH:5]=1.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C1COCC1>[Cl:18][C:19]1[N:20]=[N:21][C:22]([O:16][CH2:15][C:14]2[N:10]([C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=3)[N:11]=[N:12][C:13]=2[CH3:17])=[CH:23][CH:24]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 19914681(1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanol

생성물 1

HCID 573356983-Chloro-6-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridazine수율 95.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of sodium hydride (55%, 106 mg, 2.41 mmol) in THF (4 mL) a solution of [3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-methanol (500 mg, 2.41 mmol) in THF (6 mL) was added under ice cooling. After the addition was complete the mixture was allowed to warm up to room temperature and stirred for 30 min. Again under ice cooling a solution of 3,6-dichloropyridazine (358 mg, 2.41 mmol) in THF (6 mL) was added and the reaction mixture stirred at room temperature for 16 h. The mixture was then poured into ice water and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (735 mg, 95%) as a colourless gun. MS: m/e=3020.1 [M+H]+.

후처리

  1. additionwas added under ice cooling
  2. additionAfter the addition
  3. stirringthe reaction mixture stirred at room temperature for 16 h
  4. extractionextracted with ethyl acetate
  5. washthe combined organic extracts washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-2c8356ea2bdd472aa9c5d24c1d40ebfc
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08742097B2

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