2-Bromoethanol → HCID 68737629, compound

HRID 1878631Notes

Reaction equation

HRID 1878631 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:21][CH2:22][OH:23].[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:17][CH2:21][CH2:22][OH:23])([CH3:15])[CH3:16])=[CH:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 68934351HCID 68934351, compound2×

Product 1

HCID 68737629HCID 68737629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-(5-bromo-pyridin-3-yl)-phenyl]-1-methyl-ethylamine (Intermediate 229) (1 eq, 1.72 mmol, 500 mg) in DMF (10 ml) is added NaH (1.2 eq, 2.06 mmol, 82 mg) and the resulting mixture is stirred for 30 min at r.t. Then 2-bromoethanol (Sigma-Aldrich, St. Louis, USA) (2 eq, 3.43 mmol, 0.24 ml) is added, and the mixture is heated at 100° C. for 4 h. 2 M aqueous NaOH is added, and the mixture is extracted with DCM.

Workup

  1. temperaturethe mixture is heated at 100° C. for 4 h
  2. extractionthe mixture is extracted with DCM

Sources & evidence

ORD record
ord-0055b0fb21d848769e533e872884270f
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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