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

HRID 1396133Notes

Reaction equation

HRID 1396133 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 (6, 1 g, 2.0 mmol) in 10 mL of tetrahydrofuran, iodine (0.43 g, 1.7 mmol) in 5 mL of tetrahydrofuran is added. The reaction is stirred at room temperature overnight, then quenched with 20 mL of 1M aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layers are combined and washed with water and brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and hexanes. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound as a white solid (7, 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 and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexanes
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b0511d05efae472494e9963dba60b183
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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