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Potassium Carbonate → (3,5-Bis(trifluoromethyl)phenyl}-7-chlorofuro[2,3-c]pyridine

HRID 389487
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HRID 389487 반응식
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9](I)[O:8][C:7]=12.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.C([O-])([O-])=O.[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1.O>[F:12][C:13]([F:27])([F:28])[C:14]1[CH:15]=[C:16]([C:9]2[O:8][C:7]3=[C:2]([Cl:1])[N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=2)[CH:17]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:19]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 866624077-Chloro-2-iodofuro[2,3-c]pyridine

생성물 1

HCID 86662406(3,5-Bis(trifluoromethyl)phenyl}-7-chlorofuro[2,3-c]pyridine수율 74%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 21886435
1,4-Dioxane--water (1/1)
용매

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온도
50 °C

실험 절차

In a three-neck flask was placed a mixture of 7-chloro-2-iodofuro[2,3-c]pyridine (1.00 g, 3.58 mmol), 3,5-bis(trifluoromethyl)phenyl boronic acid (0.92 g, 3.6 mmol), 1,4-dioxane/water (50 mL/10 mL) and K2CO3 (0.74 g, 5.38 mmol). After the suspension was degassed with nitrogen for 15 min, (PPh3)2PdCl2 (0.12 g, 0.17 mmol) was added and the mixture was degassed with nitrogen for 5 min. The resultant mixture was stirred at 50° C. for 48 h under nitrogen. The mixture was then cooled to RT and the solvent was evaporated to give a black residue, which was purified by flash chromatography (2% MeOH:DCM) to afford 965 mg (74%) of the title compound as a white crystalline. 1H NMR (300 MHz, CDCl3): δ 7.06 (s, 1H), 7.50 (m, 4H), 7.94 (dd, J=1.5 Hz, 2.4 Hz, 1H), 8.19 (d, J=5.1 Hz, 1H).

후처리

  1. customIn a three-neck flask was placed
  2. customAfter the suspension was degassed with nitrogen for 15 min
  3. customthe mixture was degassed with nitrogen for 5 min
  4. temperatureThe mixture was then cooled to RT
  5. customthe solvent was evaporated
  6. customto give a black residue, which
  7. customwas purified by flash chromatography (2% MeOH:DCM)

출처 및 근거

ORD 기록
ord-c49d961a8ee54eefae68310c94485e9a
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08378104B2

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