5-Bromo-3-fluoropyridine-2-carbonitrile → 5-Cyclopropyl-3-fluoropicolinonitrile

HRID 571688ノート

反応式

HRID 571688 の反応式
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br-].[CH:12]1([Zn+])[CH2:14][CH2:13]1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([C:2]2[CH:3]=[C:4]([F:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:14][CH2:13]1

参加物

5

反応物 2

HCID 441966805-Bromo-3-fluoropyridine-2-carbonitrileHCID 178419765HCID 178419765、化合物

生成物 1

HCID 670860995-Cyclopropyl-3-fluoropicolinonitrile

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To solution of 5-bromo-3-fluoropicolinonitrile (603 mg, 3.0 mmol) and Pd(PPh3)4 (173 mg, 0.15 mmol) in 10 mL of THF was added cyclopropyl zinc bromide (0.5 M, 10 mL) under N2. After being heated 80° C. for 4 h, the mixture was cooled to room temperature and quenched with sat. NH4CL (aq). The mixture was extracted with EtOAc (3×) and the combined organic layers were washed with sat. NaHCO3 (aq.) and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel chromatography (elution with 0-8% EtOAc/Hex) to afford 5-cyclopropyl-3-fluoropicolinonitrile (406 mg).

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. customquenched with sat. NH4CL (aq)
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. washthe combined organic layers were washed with sat. NaHCO3 (aq.) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (elution with 0-8% EtOAc/Hex)

出典と根拠

ORDレコード
ord-cdcb624f93a7479b961cdca397d832e3
出典データセット
uspto-grants-2015_05
特許番号
US09029362B2

反応ノート

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