홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Water → 2-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]ethanol

HRID 1726391
노트
인쇄 미리보기

반응식

HRID 1726391 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:13][CH2:14][OH:15])[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.O.[CH2:17]([O:24]/[N:25]=[C:26]1\[CH2:27][CH2:28][C:29]2[C:34]\1=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:17]([O:24]/[N:25]=[C:26]1\[CH2:27][CH2:28][C:29]2[C:34]\1=[CH:33][CH:32]=[C:31]([C:2]1[CH:3]=[N:4][N:5]([CH2:13][CH2:14][OH:15])[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH:30]=2)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 689224722-(4-bromo-5-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanolHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid

생성물 1

HCID 876252942-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]ethanol수율 23.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
75 °C

실험 절차

To 2-(4-bromo-5-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol (0.050 g; Example 2, Step 2) dissolved in 5 mL acetonitrile was added 2 mL water, (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (0.058 g; Example 2, Step 4), and 0.155 g potassium carbonate. The mixture was purged with nitrogen and about 20 mg tetrakis(triphenyphosphine)palladium(0) catalyst was added. The mixture was heated at 75° C. After 1 hour, the reaction mixture was filtered through celite, the filter cake washed with ethyl acetate, and the filtrate evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The ethyl acetate was washed with saturated aqueous sodium carbonate, brine, dried over magnesium sulfate, filtered, and evaporated under vacuum to yield 0.05 g crude product as a colorless glass. The crude material was purified by chromatography, eluting with a mixture of 8:1 dichloromethane-methanol to afford 18.6 mg (23% yield) product as a colorless glass. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 425.2 by positive ESI.

후처리

  1. customThe mixture was purged with nitrogen and about 20 mg tetrakis(triphenyphosphine)palladium(0) catalyst
  2. additionwas added
  3. filtrationthe reaction mixture was filtered through celite
  4. washthe filter cake washed with ethyl acetate
  5. customthe filtrate evaporated under vacuum
  6. customThe residue was partitioned between ethyl acetate and water
  7. washThe ethyl acetate was washed with saturated aqueous sodium carbonate, brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customto yield 0.05 g crude product as a colorless glass
  12. customThe crude material was purified by chromatography
  13. washeluting with a mixture of 8:1 dichloromethane-methanol

출처 및 근거

ORD 기록
ord-f2cdf4a13cd946da8745921483d871cc
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07491829B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트