Sodium hydride → 6-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2378980Notes

Reaction equation

HRID 2378980 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497589456-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-chloro-1H-pyrrolo[2,3-b]pyridine (1.00 g, 6.55 mmol) in THF (1 mL) was added NaH (60%, 0.315 g, 7.86 mmoL) at 0° C. in several portions. The resulting mixture was stirred for 1 hr, followed by addition of triisopropylsilyl chloride (1.67 mL, 7.86 mmol) in neat at 0° C. The mixture was continued stirring at 0° C. under N2 for 2 hr, quenched with H2O (40 mL), and extracted with Et2O (100 mL). After separation, the organic phase was washed with brine (30 mL), dried (MgSO4), concentrated on rotary vacuo, and purified on Biotage Flash Collector eluting with 15˜30% EtOAc/Hexanes (600 mL) to afford the expected product, 6-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.51 g, 75%). 1H-NMR (400 MHz, CHLOROFORM-D) δ ppm 1.09-1.13 (m, 18 H) 1.80 (dt, J=14.92, 7.52 Hz, 3 H) 6.52 (d, J=3.53 Hz, 1 H) 7.02 (d, J=8.06 Hz, 1 H) 7.25 (d, J=3.53 Hz, 1 H) 7.77 (d, J=8.31 Hz, 1 H); Mass spec 309.19 Calc for C16H25ClN2Si 308.15.

Workup

  1. stirringThe mixture was continued stirring at 0° C. under N2 for 2 hr
  2. customquenched with H2O (40 mL)
  3. extractionextracted with Et2O (100 mL)
  4. customAfter separation
  5. washthe organic phase was washed with brine (30 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated on rotary vacuo
  8. custompurified on Biotage Flash Collector
  9. washeluting with 15˜30% EtOAc/Hexanes (600 mL)

Sources & evidence

ORD record
ord-13c62e7f69314341aed20efc6fe57ec2
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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