Benzonitrile, 3-(bromomethyl)- → 3-(2-(7-Chloroquinolin-2-yl)ethyl)benzonitrile

HRID 22599

반응식

HRID 22599 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[C:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br)#[N:22]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][CH2:26][C:25]3[CH:24]=[C:23]([CH:30]=[CH:29][CH:28]=3)[C:21]#[N:22])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 1383957-Chloro-2-methylquinolineHCID 2724682Lithium diisopropylamide

생성물 1

HCID 99945063-(2-(7-Chloroquinolin-2-yl)ethyl)benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 7-chloroquinaldine (17.7 g) in THF (80 mL) at -78° was added a solution of 100 mL lithium diisopropylamide (LDA) (1M) dropwise. After addition the solution was warmed to -20° and added dropwise to 3-cyanobenzyl bromide (20 g) in THF (80 mL) at 0°. The reaction mixture was stirred 1 hr at 0° and warmed to room temperature (30 min). The mixture was partitioned between pH 7 buffer (25% NH4OAc) and ethyl acetate. The organic layer was dried and evaporated. Flash chromatography of the residue using 30% ether in hexane afforded the title compound.

후처리

  1. additionAfter addition the solution
  2. temperaturewas warmed to -20°
  3. customThe mixture was partitioned between pH 7 buffer (25% NH4OAc) and ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated

출처 및 근거

ORD 기록
ord-0346e4d19e474aaeb7d254f608fadec3
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428171

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