1-Propanol → Ethyl 5-methyl-1-{6-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-3-carboxylate

HRID 733142ノート

反応式

HRID 733142 の反応式
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O.Cl[C:16]1[N:21]=[C:20]([N:22]2[C:26]([CH3:27])=[CH:25][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23]2)[CH:19]=[CH:18][CH:17]=1.C(O)CC.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:27][C:26]1[N:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][C:2]([F:14])([F:13])[F:1])[N:21]=2)[N:23]=[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=1

参加物

6

反応物 4

HCID 10311-PropanolHCID 516892Sodium BicarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 57428255Ethyl 1-(6-chloropyridin-2-yl)-5-methyl-1h-pyrazole-3-carboxylate

生成物 1

HCID 11361317Ethyl 5-methyl-1-{6-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-3-carboxylate収率 12.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To the solution of 2-trifluoromethoxyphenyl boronic acid (0.192 g, 0.92 mmol) and the 2-chloropyridine compound from Step 1 (0.165 g, 0.62 mmol) in toluene:n-propanol (3 mL:3 mL) were added tetrabis(triphenylphosphine)palladium (0.072 g, 0.062 mmol) and aqueous sodium bicarbonate (2.0M, 0.62 mL, 1.2 mmol). The reaction mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, the mixture was filtered through a Celite pad, and washed with ethyl acetate (3 times). The filtrate was concentrated. The resulting residue was dissolved in ethyl acetate and washed with saturated sodium carbonate aqueous solution and brine, the organic layer was dried over anhydrous sodium sulfate. After concentration, the crude product was applied to column chromatography on silica gel to afford the titled compound, as yellow oil, 30 mg, 12.3% yield.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through a Celite pad
  3. washwashed with ethyl acetate (3 times)
  4. concentrationThe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium carbonate aqueous solution and brine
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. concentrationAfter concentration

出典と根拠

ORDレコード
ord-085e1e85050440d6a9a675a51ea65a7d
出典データセット
uspto-grants-2009_09
特許番号
US07589116B2

反応ノート

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