Dichloromethane → (Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177815Notes

Reaction equation

HRID 2177815 reaction equation
Br[C:2]1[C:3]([O:31][CH3:32])=[C:4]([C:9]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2/[CH:23]=[CH:24]\[CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[O:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1.C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>O.O1CCOCC1>[CH2:27]([N:26]([CH2:29][CH3:30])[CH2:25]/[CH:24]=[CH:23]\[C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[S:13]([CH2:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:31][CH3:32])[C:2]([C:35]2[CH:36]=[CH:37][O:33][CH:34]=2)=[CH:11][CH:10]=1)(=[O:15])=[O:14])[CH3:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 66693679methyl 3-bromo-6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-2-methoxybenzoate2×

Product 1

HCID 69915014(Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-methoxybenzoate (Intermediate 161, 0.163 g), furan-3-yl boronic acid (0.041 g), palladium (II) chloride dppf complexed with DCM (0.025 g), cesium carbonate (0.282 g) in water (0.5 ml) and dioxane (3 ml) was degassed and then heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-5% to give (Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate as an orange oil.

Workup

  1. customwas degassed
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of methanol and DCM with a gradient of 0-5%

Sources & evidence

ORD record
ord-e8b1fdbcd95d496d9397e6e5ee8021c4
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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