Sodium hydride → 4-Bromo-1,6-dihydro-6-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056955Notes

Reaction equation

[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][NH:10][C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][N:10]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-bromo-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.967 g, 4.26 mmol) in N,N-dimethylformamide (30.6 mL) at 0° C. was treated with sodium hydride (0.255 g, 6.38 mmol) and stirred at 0° C. for 30 min. After this time the reaction mixture was treated with [β-(trimethylsilyl)ethoxy]methyl chloride (1.13 mL, 6.39 mmol) and subsequently stirred at 20° C. for 1 h. The reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with water (3×), dried with magnesium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes) gave the desired product (1.03 g, 68%) as a white solid. LCMS calculated for C14H22BrN2O2Si (M+H)+: m/z=357.1, 359.1. found: 357.0, 359.0.

Workup

stirringsubsequently stirred at 20° C. for 1 h
customLayers were separated
washthe organic layer was washed with water (3×)
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude residue
customPurification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-89171bbbe03247c4a5c34a6e85b309f1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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