Sodium hydride → HCID 21867524, compound

HRID 857314Notes

Reaction equation

HRID 857314 reaction equation
[Br:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:22][CH2:23][CH:24]1[O:28][CH2:27][CH2:26][O:25]1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[Br:1][C:2]1[N:3]([CH2:22][CH2:23][CH:24]2[O:28][CH2:27][CH2:26][O:25]2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 21867385HCID 21867385, compound

Product 1

HCID 21867524HCID 21867524, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a vigorously stirred solution of 0.32 g of the product from Step 2 of Example 1 in 5 mL of DMF was added sequentially 0.055 g NaH (60% in mineral oil), 0.27 mL of 2-(2-bromoethyl)-1,3-dioxolane and 0.01 g of n-Bu4NI. The mixture was stirred for 3 hours at room temperature and then quenched with 5 mL of saturated aqueous solution of NH4Cl and 5 mL of water, and extracted with 50 mL of 1:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel flash chromatography eluted with 9:1 hexane/EtOAc to give 0.3 g of the title compound as an oil.

Workup

  1. customquenched with 5 mL of saturated aqueous solution of NH4Cl and 5 mL of water
  2. extractionextracted with 50 mL of 1:1 hexane/EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-06c3047cfb3a44fab769ae1999ed859b
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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