Imidazole → 1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine

HRID 1753068Notes

Reaction equation

HRID 1753068 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:3]=1.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C(Cl)Cl>[NH3:4].[Si:25]([O:13][CH2:12][C: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)([CH3:15])[CH3:14])([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 900938832-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropan-1-ol

Product 2

HCID 222AmmoniaHCID 900934361-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridineYield 148.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropan-1-ol (Preparation 66, 3.86 g, 12.2 mmol) in DCM (50 mL) was added imidazole (2.08 g, 30.5 mmol) followed by TBDMSCl (2.21 g, 14.7 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction was partitioned between water (30 mL) and DCM (40 mL). The aqueous layer was washed twice with DCM (40 mL), the organic layers combined, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 30% EtOAc in heptanes followed by 80:20:2 EtOAc:MeOH:NH3 to afford the title compound as a colourless oil (3.90 g, 74%).

Workup

  1. customThe reaction was partitioned between water (30 mL) and DCM (40 mL)
  2. washThe aqueous layer was washed twice with DCM (40 mL)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 30% EtOAc in heptanes

Sources & evidence

ORD record
ord-5da4ee6cc143422295e829ee61334180
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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