Iodine → HCID 58112003, compound

HRID 1667616Notes

Reaction equation

HRID 1667616 reaction equation
II.Br[CH2:4][CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8].[Br:11][C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][N:23]=1)[C:15](N(OC)C)=[O:16].[NH4+].[Cl-]>C1COCC1.O>[Br:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[CH2:4][CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8])[CH:21]=[CH:22][N:23]=1

Participants

7

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 448186542-Bromo-N-methoxy-N-methylisonicotinamide

Product 1

HCID 58112003HCID 58112003, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of Mg (3.67 g, 153.01 mmol) in THF (40 mL) is added cat. Iodine, followed by a solution of 3-bromo-1,1-dimethoxy-propane (21.47 g, 117.30 mmol) in THF (40 mL). The mixture is stirred at room temperature for 2 h. Then the fresh prepared Grignard reagent is cooled down in an ice bath, and added to a solution of 2-bromo-N-methoxy-N-methyl-isonicotinamide (12.50 g, 51.00 mmol) in THF (50 mL) at 0° C. The mixture is warmed up to room temperature and stirred at this temperature for 2 h. Then the reaction mixture is cooled in an ice bath, sat. NH4Cl and water are added and the mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 10%) to give 1-(2-Bromo-pyridin-4-yl)-4,4-dimethyoxy-butane-1-one (12.1 g, 82%) as a pale yellow oil. M/Z=288.14

Workup

  1. additionis added cat
  2. temperatureis cooled down in an ice bath
  3. temperatureThe mixture is warmed up to room temperature
  4. stirringstirred at this temperature for 2 h
  5. temperatureThen the reaction mixture is cooled in an ice bath
  6. extractionthe mixture is extracted with EtOAc
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated down
  11. customThe crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 10%)

Sources & evidence

ORD record
ord-a0dc7b36f3dd44fe980c02652f290e29
Source dataset
uspto-grants-2011_10
Patent number
US08044209B2

Reaction notes

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