Sodium bis(trimethylsilyl)amide → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25785

반응식

HRID 25785 반응식
C(OC(N1C2C(=CC(C3C=CC=CC=3OC)=CC=2)C(C(O)C)=CC1(C)C)=O)(C)(C)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=[C:42]2[CH:51]([O:53][CH2:54][CH2:55][CH2:56][C:57]1C=CC=CC=1)[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CS(C)=O.C1COCC1.BrCCCC1C=CC=CC=1>[CH2:54]([O:53][CH:51]([C:42]1[C:41]2[C:46](=[CH:47][CH:48]=[C:39]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[O:32][CH3:31])[CH:40]=2)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=1)[CH3:52])/[CH:55]=[CH:56]/[CH3:57]

참가 물질

6

반응물 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 691540386-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

생성물 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline수율 61.5%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매HCID 12503(3-Bromopropyl)benzene용매

실험 절차

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (116 mg) in 2 mL of DMSO was treated with 334 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 52 μL of 1-bromo-3-phenylpropane to give the alkylated product, which was then deprotected (as above) to yield 31 mg of the title compound as an oil.

후처리

  1. customto give the alkylated product, which

출처 및 근거

ORD 기록
ord-84a4bd1588cb4f438526b2da20c9be26
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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