N-Iodosuccinimide → 3-iodo-5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

HRID 509923Notes

Reaction equation

HRID 509923 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.[I:21]N1C(=O)CCC1=O>ClCCl>[I:21][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:18]([CH3:20])[CH3:19])[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 497589615-Methyl-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 582588923-iodo-5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (8, 1.1 g, 3.8 mmol) and 10 mL of dichloromethane were combined in a round bottom flask and stirred for 10 minutes. A slurry of N-iodosuccinimide (1.0 g, 4.6 mmol) in 5 mL of dichloromethane was added and stirred at room temperature overnight. The reaction was quenched with sodium thiosulfate (20 mL, 1M in water) and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a light yellow oil (9, 1.2 g, 75%). MS (ESI) [M+H+]+=415.08.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction was quenched with sodium thiosulfate (20 mL, 1M in water)
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with ethyl acetate and hexanes
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ea2c00599d284f58a7c533addc0cc129
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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