Pyridine → 6-bromo-2-methyl-1-(2-trimethylsilanylethoxymethyl)-1H-imidazo[4,5-b]pyridine

HRID 1469099Notes

Reaction equation

HRID 1469099 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl.N1C=CC=CC=1>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:19][O:18][CH2:17][CH2:16][Si:15]([CH3:22])([CH3:21])[CH3:14])[C:9]([CH3:11])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178432051HCID 178432051, compound

Product 1

HCID 595928396-bromo-2-methyl-1-(2-trimethylsilanylethoxymethyl)-1H-imidazo[4,5-b]pyridineYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.00 g of 6-bromo-2-methyl-3H-imidazo[4,5-b]pyridine in 275 ml of tetrahydrofuran is initially introduced in a flask. 1.66 g of sodium hydride (60% in paraffin oil) are added in portions with ice-cooling. 7.00 ml of 2-trimethylsilylethoxy-methyl chloride is subsequently added dropwise at about −30° C., and the mixture is stirred at 25° C. under nitrogen until the pyridine has reacted completely (HPLC check, about 4 hours). The cooled reaction solution is added to about 200 ml of water and extracted three times with EA. The combined organic phases are dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 5-100% in 34 min.), giving 5.30 g of 6-bromo-2-methyl-1-(2-trimethylsilanylethoxymethyl)-1H-imidazo[4,5-b]pyridine as white solid (yield 40%, content 99%); MS-FAB (M+H+)=343.1; Rf (polar method): 2.59 min.

Workup

  1. temperaturecooling
  2. customhas reacted completely (HPLC check, about 4 hours)
  3. customThe cooled reaction solution
  4. extractionextracted three times with EA
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. custompurified by means of column chromatography (gradient heptane: EA 5-100% in 34 min.)

Sources & evidence

ORD record
ord-aba498eb440f49fd9651a18e1a2748ac
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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