1,2-Dibromoethane → Methyl 1-(quinolin-6-yl)cyclopropanecarboxylate

HRID 456113노트

반응식

HRID 456113 반응식
[Li+].[CH3:2][CH:3]([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:23])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.BrCCBr>C1COCC1>[CH3:9][O:10][C:11]([C:12]1([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH2:3][CH2:2]1)=[O:23]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 1514202Methyl 6-quinolineacetateHCID 2724682Lithium diisopropylamide

생성물 1

HCID 58190477Methyl 1-(quinolin-6-yl)cyclopropanecarboxylate수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of LDA (1.8 M solution in toluene, 14.8 ml, 26.6 mmol) was added dropwise to a solution of quinolin-6-yl-acetic acid methyl ester (2.14 g, 10.64 mmol) in dry THF (40 mL) under a nitrogen atmosphere at −78° C. After 30 min, 1,2-dibromoethane (2.40 g, 12.76 mmol) was added dropwise over 3 min. The resulting mixture was stirred for 1 h at room temperature, then quenched with satd aq. NH4Cl. The mixture was extracted with DCM, washed with brine, dried over Na2SO4, and stripped of solvent. The residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient to afford 463 mg (20%) of the title compound as yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.91 (dd, 1H), 8.12 (d, 1H), 8.07 (d, 1H), 7.77-7.74 (m, 2H), 7.40 (dd, 1H), 3.65 (s, 3H), 1.73-1.71 (m, 2H), 1.33-1.30 (m, 2H). LCMS (method A): [MH]+=228, tR=4.37 min.

후처리

  1. customquenched with satd aq. NH4Cl
  2. extractionThe mixture was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient

출처 및 근거

ORD 기록
ord-497dad94ce8749f68ddce116e9d12209
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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