Bromomethyl 3-methoxyphenyl ketone → HCID 67265133, compound

HRID 1684916Notes

Reaction equation

HRID 1684916 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=O.[CH3:13][C:14]1([CH3:28])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=2)[O:15]1.C(=O)([O-])O.[Na+]>C(O)CC>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:3]2[N:27]=[C:24]3[CH:23]=[CH:22][C:21]([B:16]4[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:28])([CH3:13])[O:15]4)=[CH:26][N:25]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 516892Sodium BicarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 67265133HCID 67265133, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

5.00 g of 2-bromo-1-(3-methoxyphenyl)ethanone and 4.80 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine are placed in 220 ml of n-propanol in a round-bottomed flask and 2.57 g of sodium hydrogencarbonate are added. The mixture is heated at 80° C. for 20 h and allowed to cool. The reaction mixture is concentrated under reduced pressure. The residue is taken up between water and ethyl acetate, the organic phase is separated by settling and dried over magnesium sulphate and then the solvent is concentrated. 7.47 g of compound are obtained.

Workup

  1. temperatureto cool
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe organic phase is separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationthe solvent is concentrated

Sources & evidence

ORD record
ord-f2ca54c6884740d8be4d1c38dd206d92
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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