Sodium hydride → HCID 86689864, compound

HRID 2409055Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[CH3:20][Si:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][O:16][CH2:15][N:1]1[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (618 mg, 4.32 mmol) in anhydrous THF (30 mL) at 0° C. was slowly added NaH (60% in mineral oil, 346 mg, 8.64 mmol). After stirring at 0° C. for 30 min, (2-(chloromethoxy)ethyl)trimethylsilane (865 mg, 5.19 mmol) was added followed by stirring at RT for 1 h. The reaction mixture was quenched with ice water (50 ml) and extracted with EtOAc (50 mL×3). The combined extracts were dried over (MgSO4) filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (3:1) to afford 683 mg (57.9%) of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile as a yellow solid. MS (ESI): m/z=274.2 [M+1]+.

Workup

customat 0° C.
stirringby stirring at RT for 1 h
customThe reaction mixture was quenched with ice water (50 ml)
extractionextracted with EtOAc (50 mL×3)
dry with materialThe combined extracts were dried over (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by SiO2 chromatography
washeluting with petroleum ether:EtOAc (3:1)

Sources & evidence

ORD record: ord-b1f2a6c9dc6147019812beeeccf902ea
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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