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

HRID 25786

Reaction equation

HRID 25786 reaction equation
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]/[CH:55]=[CH:56]/[C:57]1C=CC=CC=1)[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(Br)C=CC1C=CC=CC=1>C1COCC1>[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]

Participants

5

Reactant 3

HCID 98116BromomethylstyreneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 691533466-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-((E)-3-phenylallyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-((E)-3-phenylallyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 50 mg of cinnamyl bromide to give the alkylated product, which was deprotected to yield 5.8 mg of the title compound as a foam.

Workup

  1. customto give the alkylated product, which

Sources & evidence

ORD record
ord-9de8337d60034e7caad34f64ccdae3ce
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Linked notes

Loading…