p-Chlorophenacyl bromide → HCID 44232240, compound

HRID 1684911Notes

Reaction equation

HRID 1684911 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[O:3]1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=O.C(=O)([O-])O.[Na+]>C(O)CC>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:15]=[C:12]3[CH:11]=[CH:10][C:9]([B:4]4[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]4)=[CH:14][N:13]3[CH:18]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 44232240HCID 44232240, compoundYield 135.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine and 5.30 g of 2-bromo-1-(4-chlorophenyl)ethanone are placed in 150 ml of n-propanol in a round-bottomed flask. 2.67 g of sodium hydrogencarbonate are added. The mixture is heated at 80° C. for 16 h. After cooling, the reaction mixture is concentrated under reduced pressure. 10.93 g of compound are obtained, which compound is used as is in the following stages.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0be77c406661456ba60deb07698aad43
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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