Imidazole → HCID 90093728, compound

HRID 1753062Notes

Reaction equation

HRID 1753062 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:11]([CH3:14])[CH2:12][OH:13])[CH:3]=1.N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>C(Cl)Cl>[Si:24]([O:13][CH2:12][CH:11]([N:4]1[C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:2]([I:1])=[CH:3]1)[CH3:14])([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 900935552-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)propan-1-ol

Product 1

HCID 90093728HCID 90093728, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)propan-1-ol (Preparation 56, 11.5 g, 38.1 mmol) and imidazole (6.48 g, 95.2 mmol) in DCM (300 mL) was added a solution of TBDMSCl (6.95 g, 45.7 mmol) in DCM (50 mL) dropwise at 0° C. The reaction was allowed to warm to room temperature and stirred for 1.5 hours. To the reaction was added water (500 mL) and DCM (200 mL), the organic layer collected, dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-10% MeOH in DCM to afford the title compound (15 g, 100%).

Workup

  1. customthe organic layer collected
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-119a476f23304e858905730379934c04
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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