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Potassium Carbonate → 3-(3,5-Difluorophenyl)-2-ethylpyrazolo[1,5-a]pyridine

HRID 408802
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HRID 408802 반응식
[CH2:1]([C:3]1[C:11](I)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([F:20])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[C:16]([C:11]2[C:3]([CH2:1][CH3:2])=[N:4][N:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=23)[CH:17]=[C:18]([F:20])[CH:19]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 161149332-Ethyl-3-iodopyrazolo[1,5-a]pyridine

생성물 1

HCID 583793343-(3,5-Difluorophenyl)-2-ethylpyrazolo[1,5-a]pyridine수율 80%

시약·촉매·용매 3

HCID 962Water용매HCID 8857
Ethyl Acetate
용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

2-Ethyl-3-iodopyrazolo[1,5-a]pyridine (0.5 g, 2.0 mmol) and (3,5-difluorophenyl)boronic acid (0.35 g, 2.2 mmol) [Aldrich 471925] were stirred in dioxane (12 mL). A solution of potassium carbonate (0.29 g, 2.1 mmol) in water (2.8 mL) was added. Tetrakis-(triphenylphosphine)palladium(0) (0.13 g, 0.1 mmol) was added and the mixture was heated at 100° C. for 16 h. After cooling, the mixture was diluted with ethyl acetate and washed with water and brine. The extracts were dried over magnesium sulfate, filtered, concentrated and purified on silica gel with ethyl acetate in hexanes (0-10%) to give the desired compound (0.41 g, 80%). LCMS for C15H13F2N2 (M+H)+: m/z=259.2. 1H NMR (300 MHz, DMSO-d6): δ 8.67 (m, 1H), 7.64 (m, 1H), 7.25 (m, 1H), 7.18 (m, 3H), 6.90 (m, 1H), 2.89 (m, 2H), 1.22 (m, 3H).

후처리

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel with ethyl acetate in hexanes (0-10%)

출처 및 근거

ORD 기록
ord-50cdc95021744e579493276c99fbd4b0
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759359B2

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