Iodine → HCID 58191784, compound

HRID 1038657Notes

Reaction equation

HRID 1038657 reaction equation
II.Br[CH2:4][CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8].[Cl:11][C:12]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]([F:20])=[CH:14][N:13]=1.[NH4+].[Cl-]>C1COCC1.O>[Cl:11][C:12]1[CH:17]=[C:16]([CH:18]([OH:19])[CH2:4][CH2:5][CH:6]([O:9][CH3:10])[O:7][CH3:8])[C:15]([F:20])=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 447547552-Chloro-5-fluoropyridine-4-carbaldehyde

Product 1

HCID 58191784HCID 58191784, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of Mg (0.71 g, 30 mmol) in THF (10 mL) are added cat iodine and a solution of 3-bromo-1,1-dimethoxy-propane (3.99 g, 21.57 mmol) in THF (10 mL). The mixture is stirred at room temperature for 2 hours. At −30° C., to a solution of 2-chloro-5-fluoro-pyridine-4-carbaldehyde (2.0 g, 12.54 mmol) in THF (5 mL) is added to the above prepared Grignard reagent. The mixture is stirred at this temperature for 2 hours. Then the reaction mixture is cooled in an ice bath, saturated 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 chromatography (EtOAc/hexane: 10%˜40%) to give 1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-ol (0.81 g, 25%). M/Z=264.13[M+1]

Workup

  1. stirringThe mixture is stirred at this temperature for 2 hours
  2. temperatureThen the reaction mixture is cooled in an ice bath
  3. extractionthe mixture is extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customThe crude product is purified by chromatography (EtOAc/hexane: 10%˜40%)

Sources & evidence

ORD record
ord-74e4ed81c3a04b738ab1d274afbb7544
Source dataset
uspto-grants-2013_10
Patent number
US08552003B2

Reaction notes

Loading…