Sodium hydride → 4-Iodo-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

HRID 723236Notes

Reaction equation

HRID 723236 reaction equation
[I:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:11].[CH3:12][Si:13]([CH2:16][CH2:17][O:18][CH2:19]Cl)([CH3:15])[CH3:14].[H-].[Na+]>CN(C=O)C>[I:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:19][O:18][CH2:17][CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 218863944-Iodo-5-methyl-1H-benzoimidazole

Product 1

HCID 218867434-Iodo-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazoleYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Iodo-5-methyl-1H-benzoimidazole (100 mg, 0.39 mmol, Example 287: step a) and SEMCl (71 mg 0.43 mmol) in 2 mL of DMF under Ar was added NaH (11 mg, 0.43 mmol). The mixture was stirred at RT for 4 h and purified directly by PTLC (25% EtOAc/hexane) to give 122 mg (81%) of product as a colorless oil: 1H-NMR (CDCl3; 400 MHz) δ 7.95 (s, 1H), 7.37 (d, 1H, J=8.4 Hz), 7.21 (d, 1H, J=8.4 Hz), 5.48 (s, 2H), 3.47 (t, 2H, J=8.3 Hz), 2.59 (s, 3H), 0.89 (t, 2H, J=8.3 Hz), −0.06 (s, 91H). Mass spectrum (ESI, m/z): Calcd. for C14H21IN2OSi, 389.1 (M+H), found 389.0.

Workup

  1. custompurified directly by PTLC (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-9a71784bb4de4c849430f89cd80b068d
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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