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

HRID 1892404ノート

反応式

HRID 1892404 の反応式
[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>[N:19]1[C:20]2[C:15](=[CH:14][C:13]([C:12]3([C:11]([O:10][CH3:9])=[O:23])[CH2:3][CH2:2]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 nitrogen 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 rt, then quenched with saturated aqueous NH4Cl, extracted with DCM, washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient to afford the title compound as a yellow solid (463 mg, 20%). 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.

後処理

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient

出典と根拠

ORDレコード
ord-c437f11fab0c4970a2e74fb30a8f4e68
出典データセット
uspto-grants-2013_08
特許番号
US08507676B2

反応ノート

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