Imidazole → 6-Bromo-2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridine

HRID 1481702Notes

Reaction equation

HRID 1481702 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:7]=1.N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][O:12][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 15098897(6-Bromoimidazo[1,2-a]pyridin-2-yl)methanol

Product 1

HCID 712847896-Bromo-2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of (6-bromoimidazo[1,2-a]pyridin-2-yl)methanol (3.21 g, 14.13 mmol) in DCM (50 mL) was added imidazole (1.30 g, 19.09 mmol) followed by TBSCl (2.60 g, 17.25 mmol). Reaction mixture was stirred at room temperature for 30 min then was diluted with DCM (50 mL) and washed with H2O (50 mL). Organic phase was washed with NaCl (aqueous saturated, 50 mL) and dried over Na2SO4. Solvent was concentrated and residue purified by column chromatography using EtOAc/hexanes (gradient 0-50%) to afford 6-bromo-2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridine (3.32 g) in 69% yield as pale yellow solid.

Workup

  1. customReaction mixture
  2. washwashed with H2O (50 mL)
  3. washOrganic phase was washed with NaCl (aqueous saturated, 50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationSolvent was concentrated
  6. customresidue purified by column chromatography

Sources & evidence

ORD record
ord-0aee9ea0144641f7addfc5121ad05b2a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…