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

HRID 1486652노트

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HRID 1486652 반응식
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

참가 물질

5

반응물 2

HCID 441966805-Bromo-3-fluoropyridine-2-carbonitrileHCID 178419765HCID 178419765, 화합물

생성물 1

HCID 670860995-Cyclopropyl-3-fluoropicolinonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9ee13b790f23493e956dece278d06826
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428475B2

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