Sodium bis(trimethylsilyl)amide → HCID 10005864, compound

HRID 25794Notes

Reaction equation

HRID 25794 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)CCO.BrC1C=C([CH2:18][CH2:19][O:20][CH:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[O:39][CH3:40])[CH:31]=3)[NH:26][C:25]([CH3:42])([CH3:41])[CH:24]=2)[CH3:22])C=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(OC(N1C2C(=CC(C3C=CC=CC=3OC)=CC=2)C(C(OS(C)(=O)=O)C)=CC1(C)C)=O)(C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:8]=[CH:9][C:10]=1[CH2:18][CH2:19][O:20][CH:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])[CH:31]=2)[NH:26][C:25]([CH3:42])([CH3:41])[CH:24]=1)[CH3:22]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 207603354-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterHCID 691537604-{1-[2-(3-Bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 3-Bromophenethyl alcohol

Product 1

HCID 10005864HCID 10005864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{1-[2-(3-Bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 3-Bromophenethyl alcohol (37 μL) was treated with 277 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 86 mg of 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester to give alkylated product, which was deprotected to yield 13.6 mg of the title compound as a foam.

Workup

  1. customto give alkylated product, which

Sources & evidence

ORD record
ord-7b7c347ecd19433da37959625102c43d
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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