2-Chloroisoquinoline → 2-Phenylisoquinoline

HRID 1795385

반응식

HRID 1795385 반응식
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[N:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1>C1COCC1>[C:1]1([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 219893902-ChloroisoquinolineHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 53205292-Phenylisoquinoline수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of phenylmagnesium bromide (1M in THF, 3.6 mL, 3.6 mmol) is added to a solution of 2-chloro-isoquinoline (258 mg, 1.57 mmol)) and Fe(acac)3 (28 mg, 0.078 mmol) in THF (10 mL) at −30° C. After stirring for 50 min at that temperature, the reaction is quenched with brine, the aqueous layer is extracted with Et2O, the combined organic phases are dried over Na2SO4 and evaporated, and the residue is purified by flash chromatography (hexane/ethyl acetate, 10:1). After eluting a first fraction containing biphenyl (60 mg), one obtains 2-phenyl-isoquinoline as a colorless solid (184 mg, 57%). 1H NMR (300 MHz, CD2Cl2) δ 8.60 (d, 1H), 8.11 (d, 1H), 7.91 (d, 1H), 7.66–7.72 (m, 4H), 7.48–7.57 (m, 4H); 13C NMR (75 MHz, CD2Cl2) δ 160.9, 142.6, 140.1, 137.2, 130.3, 130.2, 128.8, 128.5, 127.7, 127.5, 127.3, 127.0, 120.1.

후처리

  1. customthe reaction is quenched with brine
  2. extractionthe aqueous layer is extracted with Et2O
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customthe residue is purified by flash chromatography (hexane/ethyl acetate, 10:1)
  6. washAfter eluting a first fraction
  7. additioncontaining biphenyl (60 mg), one

출처 및 근거

ORD 기록
ord-568248c7f9ff402b803e549a0741a8cc
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026478B2

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