Triisopropylsilyl trifluoromethanesulfonate → 4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 733068Notes

Reaction equation

HRID 733068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Li]CCCC.[Si:16](OS(C(F)(F)F)(=O)=O)([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:9]=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (3.21 g, 21 mmol) in THF (60 mL), cooled at −78° C., is added slowly n-BuLi (1.6 M in hexane, 13.8 mL, 22 mmol). After stirring for 30 minutes, the TIPSOTf (5.77 mL, 21.4 mmol) is added. The mixture is allowed to rise to room temperature and quenched with water. The mixture is partitioned between hexanes (200 mL) and brine. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluting with hexanes) to afford the title compound: 1H NMR 600 MHz (Acetone-d6) δ 8.19 (d, 1H, J=5.4 Hz), 7.57 (d, 1H, J=3.0 Hz), 7.18 (d, 1H, J=5.4 Hz), 6.69 (d, 1H, J=3.0 Hz), 1.92 (sept, 3H, J=7.2 Hz), 1.12 (d, 18H, J=7.2 Hz); MS m/z 309.2 (M+1).

Workup

  1. customto rise to room temperature
  2. customquenched with water
  3. customThe mixture is partitioned between hexanes (200 mL) and brine
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography (silica gel, eluting with hexanes)

Sources & evidence

ORD record
ord-310893fbaa9f43b3a98060e826d47b56
Source dataset
uspto-grants-2009_09
Patent number
US07589101B2

Reaction notes

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