Water → 6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl 2,2-dimethylpropionate

HRID 40486

반응식

HRID 40486 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].[C:21]([O:27][CH2:28]I)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23].O>CN(C=O)C>[CH3:23][C:22]([CH3:25])([CH3:24])[C:21]([O:27][CH2:28][N:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:6][C:7]1=[O:12])=[O:26]

참가 물질

6

반응물 4

HCID 962Water2회HCID 10796Cesium carbonateHCID 104401Iodomethyl pivalate2회HCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 580317186-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl 2,2-dimethylpropionate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1.0 g of 6-bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one was dissolved in 10 ml of dry DMF, 3.85 g of cesium carbonate were added and 953 mg of iodomethyl pivalate were added dropwise while cooling with water, and the mixture was stirred at room temperature for 4 hours. The experiment was left to stand at room temperature overnight. Then a further 0.4 ml of iodomethyl pivalate was added at room temperature and the mixture was stirred at room temperature for a further 2 hours. (According to TLC and LC-MS, there is still reactant in the reaction solution). 50 ml of water were added, the mixture was extracted three times with 50 ml each time of ethyl acetate. The combined organic phases were dried over MgSO4, then concentrated under reduced pressure and purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate. This gave 700 mg of 6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl 2,2-dimethylpropionate.

후처리

  1. waitThe experiment was left
  2. waitto stand at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for a further 2 hours
  4. extractionthe mixture was extracted three times with 50 ml each time of ethyl acetate
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate

출처 및 근거

ORD 기록
ord-ac61da003d14440fb1dc6c3dc0550b73
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530413B2

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