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

HRID 714270

反応式

HRID 714270 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-137027e8b7ad4a3db17e10c285d744ef
出典データセット
uspto-grants-2015_11
特許番号
US09187424B1

関連ノート

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