Butyl vinyl ether → HCID 118199865, compound

HRID 633768Notes

Reaction equation

HRID 633768 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([F:11])[F:10])=[N:6][CH:7]=1.[CH3:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]=[CH2:18].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:15]([O:16][C:17]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([F:11])[F:10])=[N:6][CH:7]=1)=[CH2:18])[CH2:14][CH2:13][CH3:12]

Participants

8

Reactant 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 498534165-Bromo-2-(difluoromethoxy)pyridine

Product 1

HCID 118199865HCID 118199865, compoundYield 10.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

1 g (4.46 mmol) of 5-bromo-2-difluoromethoxypyridine in 20 mL of H2O/DMF (1/4: v/v), 1.46 mL (11.16 mmol) of N-butyl vinyl ether, 30.68 mg (0.13 mmol) of palladium(II) acetate, 125 mg (0.29 mmol) of 1,3-bis(diphenylphosphino)propane and 746 mg (5.36 mmol) of potassium carbonate are placed in a microwave tube. After microwave irradiation for 1 hour at 120° C., the crude product is taken up in water and extracted with DCM. The organic phase is dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 0/100 EtOAc/heptane to 20/80 EtOAc/heptane over 35 minutes) to give 110 mg of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine, corresponding to the following characteristics:

Workup

  1. customAfter microwave irradiation for 1 hour at 120° C.
  2. extractionextracted with DCM
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on silica gel (eluent: 0/100 EtOAc/heptane to 20/80 EtOAc/heptane over 35 minutes)

Sources & evidence

ORD record
ord-1fa6d819e69744f3a8139099ae0a2087
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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