1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole → {2-amino-3-nitro-6-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyridin-4-yl}-benzyl-carbamic acid ethyl ester

HRID 639665Notes

Reaction equation

HRID 639665 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[CH2:14]([O:16][C:17](=[O:37])[N:18]([C:26]1[CH:31]=[C:30](Br)[N:29]=[C:28]([NH2:33])[C:27]=1[N+:34]([O-:36])=[O:35])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:15]>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[CH2:14]([O:16][C:17](=[O:37])[N:18]([C:26]1[CH:31]=[C:30]([C:8]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:13])([CH3:12])[CH3:1])[CH:11]=[CH:10][N:9]=2)[N:29]=[C:28]([NH2:33])[C:27]=1[N+:34]([O-:36])=[O:35])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:15]

Participants

4

Reactant 2

HCID 110526051-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazoleHCID 86614485(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Product 1

HCID 67456488{2-amino-3-nitro-6-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyridin-4-yl}-benzyl-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 84124Bis(triphenylphosphine)palladium chlorideCatalyst

Procedure

The title compound was prepared following the example in preparation 70, using 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (201 mg), (2-amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester (200 mg) and palladium bis(triphenylphosphine)dichloride (71 mg), giving the product (174 mg) as a yellow gum.

Workup

  1. customin preparation 70

Sources & evidence

ORD record
ord-f35d3c9b0d324b36981b54c4318a0dae
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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