Potassium Carbonate → HCID 67246338, compound

HRID 1775412Notes

Reaction equation

HRID 1775412 reaction equation
O.[SH-:2].[Na+].C([O-])([O-])=O.[K+].[K+].Br[CH2:11][C:12](=[O:15])[CH2:13][CH3:14].Br[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH:23]=O>O.CN(C=O)C>[S:2]1[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:23]=[C:11]1[C:12](=[O:15])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 111167404-Bromopyridine-3-carbaldehydeHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 67246338HCID 67246338, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydrosulfide hydrate (1.31 g, 17.7 mmol) in 5 mL water was added DMF (30 mL) and K2CO3 (3.27 g, 23.7 mmol). The mixture was cooled to 0° C. in an ice bath before adding 1-bromo-2-butanone (2.68 g, 17.7 mmol). After 15 minutes, a solution of 4-bromopyridine-3-carbaldehyde (2.20 g, 11.8 mmol) in DMF (20 mL) was added. The reaction mixture was stirred at 45° C. for 2.5 days. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, and evaporated to give the crude product (1.80 g, 80%) which was used in the next step without further purification. MS m/z 192 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-7be4da68fd714222ada8474e83ee557d
Source dataset
uspto-grants-2016_02
Patent number
US09260450B2

Reaction notes

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