Bromide ion → HCID 57660935, compound

HRID 1424318Notes

Reaction equation

HRID 1424318 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][CH:18]1[CH2:22][NH:21][C:20](=[O:23])[CH2:19]1.[H-].[Na+].[Na].[Br-]>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1)[CH2:17][CH:18]1[CH2:19][C:20](=[O:23])[NH:21][CH2:22]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 24758Sodium hydrideHCID 5360545SodiumHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 179489684-(broMoMethyl)-2-Pyrrolidinone

Product 1

HCID 57660935HCID 57660935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Methylpyridin-2-yl)carbamic acid tert-butyl ester was alkylated with 4-bromomethylpyrrolidin-2-one by deprotonation in DMF at 0° C. with NaH and treating the sodium salt with the bromide at room temperature. After dilution of the reaction mixture with ethyl acetate and washing with saturated aqueous NaHCO3 the crude product was purified by chromatography on silica gel (ethyl acetate/hexane) to yield (14) as yellow oil.

Workup

  1. washAfter dilution of the reaction mixture with ethyl acetate and washing with saturated aqueous NaHCO3 the crude product
  2. customwas purified by chromatography on silica gel (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac31adea32784761bff93c5d37baa03f
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

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