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Potassium Carbonate → benzyl 4-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]piperidine-1-carboxylate

HRID 1726399
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HRID 1726399 반응식
Br[C:2]1[C:3](C2C=CN=CC=2)=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH2:8]2)[CH:6]=1.[CH2:29]([O:36]/[N:37]=[C:38]1\[CH2:39][CH2:40][C:41]2[C:46]\1=[CH:45][CH:44]=[C:43](B(O)O)[CH:42]=2)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:29]([O:36]/[N:37]=[C:38]1\[CH2:39][CH2:40][C:41]2[C:46]\1=[CH:45][CH:44]=[C:43]([C:2]1[CH:3]=[N:4][N:5]([CH:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:14])[CH2:11][CH2:12]3)[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH:42]=2)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 68923615benzyl 4-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylateHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid

생성물 1

HCID 87625891benzyl 4-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]piperidine-1-carboxylate수율 166.1%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To benzyl 4-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (0.32 g; Example 5, Step 1) in 10 mL acetonitrile and 3 mL water was added 0.315 g (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (prepared as described in example 2, step 4) and 0.30 g potassium carbonate. The reaction mixture was purged with nitrogen and 84 mg tetrakis(triphenyphosphine)palladium(0) catalyst was added. The reaction mixture heated to 80° C. for 2 hours, filtered through celite, and the filter cake was washed with acetonitrile. The filtrate was evaporated under vacuum to yield crude product. The residue was purified by chromatography, eluting with ethyl acetate to afford 0.36 g (83% yield) product as a colorless oil. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 598.3 by positive ESI.

후처리

  1. customThe reaction mixture was purged with nitrogen and 84 mg tetrakis(triphenyphosphine)palladium(0) catalyst
  2. additionwas added
  3. filtrationfiltered through celite
  4. washthe filter cake was washed with acetonitrile
  5. customThe filtrate was evaporated under vacuum
  6. customto yield crude product
  7. customThe residue was purified by chromatography
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-0993941776bf4191adb782890b2a9cdc
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07491829B2

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