Butyl vinyl ether → HCID 86704186, compound

HRID 1497642Notes

Reaction equation

HRID 1497642 reaction equation
Br[C:2]1[C:3]([F:23])=[C:4]([N:8]([CH2:20][O:21][CH3:22])[S:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:53]([O:57][CH:58]=[CH2:59])[CH2:54][CH2:55][CH3:56]>C(O)CO.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:53]([O:57][C:58]([C:2]1[C:3]([F:23])=[C:4]([N:8]([CH2:20][O:21][CH3:22])[S:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[CH2:59])[CH2:54][CH2:55][CH3:56]

Participants

7

Reactant 3

HCID 8108Butyl vinyl etherHCID 812191,3-Bis(diphenylphosphino)propaneHCID 66729400HCID 66729400, compound

Product 1

HCID 86704186HCID 86704186, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6.15 g (15 mmol) of N-(3-bromo-2-fluorophenyl)-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide in 35 mL of ethylenglycol in a flask equipped with a rubber septum, through which nitrogen is fluxed by a needle, 37.5 mg (0.15 mmol) of palladium acetate, 129 mg (0.30 mmol) of DPPP, 5.4 mL (37.5 mmol) of TEA and 5.9 mL (45 mmol) of n-butylvinylether were added consecutively. The mixture was heated at 120° C. under stirring for 6 h and then diluted with DCM and washed with brine. The organic layer was dried over Na2SO4 and evaporated, giving N-[3-(1-butoxyethenyl)-2-fluorophenyl]-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide as a brown oil. The latter, without any further purification, was dissolved in 65 mL of 1,4-dioxane and 11 mL of 1N HCl were added to the resulting solution. After 1 h under stirring at r.t. the reaction was complete. The solvent was then removed, the residue re-dissolved with DCM and washed with aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and evaporated. After trituration with diethylether 4.82 g (86%) of the title compound were collected by filtration.

Workup

  1. additionwere added consecutively
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-69f907708eae4713864bb29986b9c3f1
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

Loading…