Hexane → 4-Iodo-1-(5,5,5-trifluoropentyl)-1H-pyrazole

HRID 1629776

反応式

HRID 1629776 の反応式
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15].CCCCCC>CN(C=O)C.O.CCOCC>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:6]=1

参加物

8

反応物 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 770224-IodopyrazoleHCID 5803495-Bromo-1,1,1-trifluoropentane

生成物 1

HCID 866858664-Iodo-1-(5,5,5-trifluoropentyl)-1H-pyrazole収率 83.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-iodo-1H-pyrazole (337 mg, 1.737 mmol) in DMF (10 mL) was added sodium hydride (104 mg, 2.61 mmol). After 30 min, 5-bromo-1,1,1-trifluoropentane (427 mg, 2.085 mmol) was added. The reaction was stirred at rt for 2 h. 3:1 hexane:ether and water were added. The organic layer was washed with H2O, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (24 g silica gel, eluted with 0-60% EtOAc in hexanes) to give the desired product (460 mg, 83%) as clear oil. LCMS Anal. Calc'd for C8H10F3IN2 318.0, found [M+H] 319.0. 1H NMR (400 MHz, CDCl3) δ 7.49 (s, 1H), 7.40 (s, 1H), 4.12 (t, J=6.9 Hz, 2H), 2.00-2.15 (m, 2H), 1.85-1.96 (m, 2H), 1.47-1.61 (m, 2H).

後処理

  1. washThe organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (24 g silica gel, eluted with 0-60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9289486a6f2841a692d05aeaab429b84
出典データセット
uspto-grants-2014_07
特許番号
US08791091B2

関連ノート

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