Sodium hydride → HCID 57500375, compound

HRID 2273543Notes

Reaction equation

HRID 2273543 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6].[H-].[Na+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C)C=O.C(OCC)(=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:5]([C:4]1[CH:3]=[C:2]([CH:17]=[CH:16][CH:15]=1)[O:1][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:6]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 28394124HCID 28394124, compound

Product 1

HCID 57500375HCID 57500375, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

23.8 g (0.10 mol) of 3-hydroxy-N-(pyridin-2-ylmethyl)-benzamide (stage B of Example 42) are added portionwise to the suspension of 4.5 g (0.10 mol) of sodium hydride (55% dispersion in oil) in 400 ml of N,N-di-methylformamide at 0° C. under argon, followed, after 10 minutes, by 15.4 ml (0.10 mol) of tert-butyl 2-bromo-acetate. The mixture is stirred at ambient temperature for 1 hour. The reaction medium is diluted with ethyl acetate and extracted with water. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The white solid is taken up in diisopropyl ether, filtered and dried, to give 26.3 g (74%) of a beige powder.

Workup

  1. extractionextracted with water
  2. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-20b3bf8fea0f4c409903554efc2d1cc8
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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