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Potassium Carbonate → 4-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

HRID 516630
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HRID 516630 반응식
C([O-])(O)=O.[Na+].[CH:6]1(B(O)O)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1I)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1[CH:6]1[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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6

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HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 594971024-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one

생성물 1

HCID 594971164-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

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온도
175 °C

실험 절차

NaHCO3 (1.0 g, excess), cyclopropylboronic acid (0.74 g, 8.93 mmol), potassium carbonate (1.23 g, 8.93 mmol) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II)-DCM complex (0.36 g, 0.45 mmol) were added to a solution of intermediate D10 (1.0 g, 2.98 mmol) in 1,4-dioxane (10 ml). The resulting mixture was heated at 175° C. for 20 minutes under microwave irradiation, after which it was filtered through diatomaceous earth and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo yielding D34 (0.6 g, 69%).

후처리

  1. filtrationafter which it was filtered through diatomaceous earth
  2. customthe solvent was evaporated in vacuo
  3. customThe crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
  4. customThe desired fractions were collected
  5. customevaporated in vacuo
  6. customyielding D34 (0.6 g, 69%)

출처 및 근거

ORD 기록
ord-845de4cedd0046eaa462aadd49d1e39e
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09114138B2

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