Iodine → 3-Iodo-5-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 509924Notes

Reaction equation

HRID 509924 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.[I:21]I>O1CCCC1>[I:21][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 807IodineHCID 497589615-Methyl-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 467367383-Iodo-5-methyl-1H-pyrrolo[2,3-b]pyridineYield 4.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (8, 1 g, 2.0 mmol) in 10 mL of tetrahydrofuran, iodine (0.43 g, 1.7 mmol) in 5 mL of tetrahydrofuran was added. The reaction was stirred at room temperature overnight, then quenched with 20 mL of 1M aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layers were combined and washed with water, brine, dried over 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 white solid (10, 20 mg). MS (ESI) [M+H+]+=258.70.

Workup

  1. customquenched with 20 mL of 1M aqueous sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexanes
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8bf66595f4004bbbb9342e57d22df197
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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