Methyl iodide → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515918Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.[CH2:18]([Li])CCC.CCCCCC.CI>O1CCCC1>[C:14]([Si:11]([CH3:13])([CH3:12])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH3:18])[CH:3]=[C:4]2[CH:10]=[CH:9]1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution 5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 7, 10.0 g, 32.2 mmol) in anhydrous tetrahydrofuran (200 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 19.3 mL, 48.2 mmol) dropwise. After stirring for 20 min at −78° C., methyl iodide (13.72 g, 96.6 mmol) was added. The resulting mixture was stirred for 2 h, quenched with a saturated ammonium chloride solution (50 mL), extracted with ethyl acetate (2×200 mL), dried over anhydrous sodium sulfate, concentrated in vacuo to give 1-(tert-butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine (7.92 g, 100%) which was used in the next step without purification: LC/MS m/e calcd for C14H22N2Si [M+H]+ 247.43, observed 247.0.

Workup

stirringThe resulting mixture was stirred for 2 h
customquenched with a saturated ammonium chloride solution (50 mL)
extractionextracted with ethyl acetate (2×200 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4c4a2f1a0aa943659e266f29926558d2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

Loading…