Sodium hydride → 7-Iodo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[4,3-b]pyridine

HRID 1522578Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12.[H-].[Na+].Cl[CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:3]=12

Participants

Conditions

Temperature: 0 °C

Procedure

7-Iodo-1H-pyrazolo[4,3-b]pyridine (1.5 g, 6.12 mmol) was dissolved in dry DMF (51.0 mL), cooled to 0° C. and NaH (0.245 g, 60% in oil, 6.12 mmol) was added. After 15 minutes and (2-(chloromethoxy)ethyl)trimethylsilane (1.080 mL, 6.12 mmol) was added and the mixture was warmed to room temperature over 2 hours then poured into ice water (350 mL) to give a solid which was filtered off. The filtrate was combined with dichloromethane and evaporated onto silica gel. Silica gel chromatography eluted with 0-5% MeOH in DCM gave 7-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-b]pyridine.

Workup

temperaturethe mixture was warmed to room temperature over 2 hours
customto give a solid which
filtrationwas filtered off
customevaporated onto silica gel
washSilica gel chromatography eluted with 0-5% MeOH in DCM

Sources & evidence

ORD record: ord-43bff6cca9614455a159cd53687fb448
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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