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

HRID 389487
ノート
印刷プレビュー

反応式

HRID 389487 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒
HCID 21886435
1,4-Dioxane--water (1/1)
溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c49d961a8ee54eefae68310c94485e9a
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08378104B2

反応ノート

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