Sodium Bicarbonate → HCID 68638439, compound

HRID 2196453Notes

Reaction equation

HRID 2196453 reaction equation
Br[CH:2]([CH3:10])[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=O.C(=O)([O-])O.[Na+].[Si:16]([O:23][CH2:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:32]=[CH:33][C:34]([NH2:37])=[N:35][CH:36]=2)[CH:28]=[CH:29][CH:30]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(O)C>[Si:16]([O:23][CH2:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:32]=[CH:33][C:34]3[N:35]([C:2]([CH3:10])=[C:3]([C:5]4[S:6][CH:7]=[CH:8][CH:9]=4)[N:37]=3)[CH:36]=2)[CH:28]=[CH:29][CH:30]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 117699522-Bromo-1-(thiophen-2-yl)propan-1-oneHCID 442323785-[3-(tert-Butyldimethylsilanyloxymethyl)phenyl]pyridin-2-ylamine

Product 1

HCID 68638439HCID 68638439, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

In a glass tube, 280 mg of 5-[3-(tert-butyldimethylsilanyloxymethyl)phenyl]pyridin-2-ylamine, 390 mg of 2-bromo-1-thiophen-2-ylpropan-1-one and 190 mg of sodium hydrogencarbonate are dissolved in 5 ml of ethanol. The tube is closed and heated at 100° C. for 20 h. After cooling, the mixture is concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 260 mg of compound are obtained.

Workup

  1. customThe tube is closed
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-74952a896aff4453826db99d96a0be16
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

Loading…