Iodine → HCID 69212831, compound

HRID 2375766Notes

Reaction equation

HRID 2375766 reaction equation
II.Br[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Br[C:13]1[N:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1>C1COCC1.[Cl-].[NH4+].[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][C:8]([O:7][C:5](=[O:6])[CH2:4][C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][N:18]=1)([CH3:11])[CH3:10]

Participants

8

Reactant 3

HCID 807IodineHCID 79177tert-Butyl bromoacetateHCID 50057186-Bromopyridine-3-carbonitrile

Product 1

HCID 69212831HCID 69212831, compoundYield 43.1%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

0.715 g (10 mmol) of zinc, a few flakes of iodine and 0.845 ml (5.4 mmol) of t-butyl bromoacetate in 10 ml of THF are introduced into a microwave reactor. The mixture is heated by microwaves for 5 min at 110° C. and then filtered and added to a solution of 0.5 g (2.7 mmol) of 6-bromo-3-pyridinecarbonitrile in 15 ml of THF. 316 mg of tetrakis(triphenylphosphine)palladium are added and the reaction mixture is heated by microwaves at 120° C. for 5 min, with stirring, and then cooled, diluted with ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and then dried over magnesium sulfate and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel using a methylcyclohexane/ethyl acetate mixture (9/1; v/v) as the eluent to give 254 mg of the expected product in the form of a yellow solid (yield=43%).

Workup

  1. filtrationfiltered
  2. temperaturethe reaction mixture is heated by microwaves at 120° C. for 5 min
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product obtained
  9. customis purified by chromatography on silica gel using a methylcyclohexane/ethyl acetate mixture (9/1; v/v) as the eluent

Sources & evidence

ORD record
ord-7d108913d33c4a3ca81b60bb71f34885
Source dataset
uspto-grants-2008_12
Patent number
US07465811B2

Reaction notes

Loading…