Sodium hydride → 5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 253465Notes

Reaction equation

HRID 253465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15]>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 242292205-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 580879285-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 88.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (150, 31.2 g, 0.112 mol) was dissolved in N-methylpyrrolidinone (800 mL) and NaH (60% dispersion, 4.93 g, 0.123 mol) was added at room temperature. The resulting mixture was stirred for 30 minutes. To this mixture was then added triisopropylsilylchloride (24.0 mL, 0.112 mol) and the resulting mixture was stirred for 2 hours. The reaction was quenched with water and extracted with ethyl acetate three times, washed by brine, dried, filtered, and concentrated in vacuo. The residue was subjected to silica gel flash chromatography (eluted by heptane to 5% ethyl acetate/heptane) to afford the desired compound (43 g 88%) as a pale-yellow solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate three times
  3. washwashed by brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was subjected to silica gel flash chromatography (eluted by heptane to 5% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-166bb7ba0bab4fd4acea726ae3cf269f
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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