Reaktion #1611575

Reaktionsgleichung

Triisopropylsilyl chloride

N2

6-bromo-1H-pyrrolo[2,3-b]pyridine

sodium hydride

→

6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Ausbeute 55.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a yellow solution
2. 2
   workup.STIRRINGthe mixture was stirred for 30 min
3. 3
   Einengenbefore being concentrated in vacuo
4. 4
   Extraktionextracted with DCM (3×)
5. 5
   TrocknenThe combined organic extracts were dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product was purified by chromatography on silica gel (0 to 10% EtOAc/Heptane)

Vorschrift

A 200-mL round-bottom flask was charged with 6-bromo-1H-pyrrolo[2,3-b]pyridine (2.961 g, 15.03 mmol) and THF (30 ml) to give a yellow solution. The flask was fitted with an N2 sweep, then sodium hydride (60% disperion in mineral oil) (0.721 g, 18.03 mmol) was added over 2 min, and the resulting mixture was stirred for 40 min. Triisopropylsilyl chloride (4.02 ml, 18.79 mmol) was added in one portion, and the mixture was stirred for 30 min before being concentrated in vacuo. The residue was taken up in saturated aq. sodium bicarbonate solution and extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (0 to 10% EtOAc/Heptane) to give 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (2.952 g, 8.35 mmol, 55.6% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ=7.72 (d, J=8.1 Hz, 1 H), 7.26 (d, J=3.5 Hz, 1 H), 7.18 (d, J=8.1 Hz, 1 H), 6.53 (d, J=3.5 Hz, 1 H), 1.81 (spt, J=7.5 Hz, 3 H), 1.13 (d, J=7.5 Hz, 18 H).

Quelle