Sodium hydride → 4-Cyano-6-(2,4-difluorobenzyloxy)-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine

HRID 582021

반응식

HRID 582021 반응식
[H-].[Na+].[F:3][C:4]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].[C:13]([C:15]1[CH:20]=[C:19]([O:21][C:22]2[N:26]([CH3:27])[N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[N:18]=[C:17](OC2N(C)N=C(C(F)(F)F)C=2)[CH:16]=1)#[N:14]>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[C:13]([C:15]1[CH:16]=[C:17]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([F:12])=[CH:11][C:4]=2[F:3])[N:18]=[C:19]([O:21][C:22]2[N:26]([CH3:27])[N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:20]=1)#[N:14]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 918672,4-Difluorobenzyl alcoholHCID 540602494-Cyano-2.6-bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine

생성물 1

HCID 539469654-Cyano-6-(2,4-difluorobenzyloxy)-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine수율 21.2%

시약·촉매·용매 2

HCID 31347Sulfolane용매HCID 22335286Ethyl acetate pentane용매

반응 조건

온도
90 °C

실험 절차

Sodium hydride (0.1 g, 60%, 2.5 mmol) is added to a solution of 2,4-difluorobenzyl alcohol (0.28 ml, 2.5 mmol) in sulfolane (5 ml) at 50° C. After 1 hour at 50° C., 4-cyano-2,6-bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine (1 g, 2.3 mmol) (from Example 2) is added to the reaction mixture. The mixture is heated to 90° C. overnight. After cooling, the reaction mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 6 times with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 8/2 v/v) and washing of the product with diisopropyl ether yields the title compound (0.2 g, 21% yield) of melting point 109° C.

후처리

  1. temperatureAfter cooling
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed 6 times with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 8/2 v/v)
  8. washwashing of the product with diisopropyl ether

출처 및 근거

ORD 기록
ord-2dc9f3a0f29348f887ce316afa20cb33
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922738

연결된 노트

불러오는 중…