Sodium hydride → 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine

HRID 246481Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 7-bromo-1H-pyrrolo[2,3-c]pyridine (0.2 g, 1.02 mmol) in DMF (5 mL), cooled to 0° C., was added sodium hydride (46.7 mg, 1.17 mmol). After 10 min the mixture was warmed to 25° C. After 20 min the mixture was recooled to 0° C. and (2-(chloromethoxy)ethyl)trimethylsilane (186 mg, 1.12 mmol) added drop-wise. After 5 min the mixture was warmed to 25° C. After 20 min the mixture was partitioned between ethyl acetate and water. The organic phase was washed with water then concentrated in vacuo. Purification by chromatography (silica, 12 g Analogix column, 0-8% ethyl acetate in hexanes) gave 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine (0.28 g, 84%) as a colorless oil.

Workup

temperatureAfter 5 min the mixture was warmed to 25° C
customAfter 20 min the mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with water
concentrationthen concentrated in vacuo
customPurification by chromatography (silica, 12 g Analogix column, 0-8% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-78677bea67a646aa9ba29b4b70cfdefe
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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