Water → HCID 86663521, compound

HRID 2406569Notes

Reaction equation

HRID 2406569 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=1.[C:16]([CH2:18][C:19]([NH:21][CH:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:26]=1)[CH2:23][CH3:24])=[O:20])#[N:17].O>CS(C)=O>[Br:7][C:8]1[N:13]=[C:12](/[CH:14]=[C:18](\[C:16]#[N:17])/[C:19]([NH:21][CH:22]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:29][CH:30]=2)[CH2:23][CH3:24])=[O:20])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27570096-Bromopyridine-2-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 66822304HCID 66822304, compound

Product 1

HCID 86663521HCID 86663521, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (0.014 g, 0.127 mmol) was added to a stirred solution of 6-bromo-2-pyridinecarboxaldehyde (0.094 g, 0.51 mmol) and 2-cyano-N-(1-(4-(2-methoxyethoxy)-phenyl)propyl)acetamide (0.07 g, 0.25 mmol) in dimethylsulfoxide (10 mL) under nitrogen at room temperature. After 26 hours the mixture was shaken with water and then extracted with ethyl acetate several times. The combined extracts were washed with water and then dried over sodium sulfate. The solvent was removed in vacuo leaving 0.10 g of a clear amber syrup, which was flash chromatographed on a column (5×10 cm) of silica gel with gradient elution utilizing dichloromethane/EtOAc (10:0 gradually changing to 12:1) to afford 0.040 g of the product as a clear pale yellow syrup; mass spec ES+m/z=444, 466 (m+1, m+23).

Workup

  1. extractionextracted with ethyl acetate several times
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-23f04cb8f5c94f829f8c9fa046fc1d06
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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