Dichloromethane → 4-(4'-Difluoromethoxy-biphenyl-4-ylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 2266849Notes

Reaction equation

HRID 2266849 reaction equation
ClCCl.[CH3:4][O:5][C:6]([C:8]1[O:9][C:10]([CH3:30])=[C:11]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)[CH:12]=1)=[O:7].[F:31][CH:32]([F:41])[O:33][C:34]1[CH:39]=[CH:38][C:37](I)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:4][O:5][C:6]([C:8]1[O:9][C:10]([CH3:30])=[C:11]([CH2:13][S:14][C:15]2[CH:16]=[CH:17][C:18]([C:37]3[CH:38]=[CH:39][C:34]([O:33][CH:32]([F:41])[F:31])=[CH:35][CH:36]=3)=[CH:19][CH:20]=2)[CH:12]=1)=[O:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27370081-(Difluoromethoxy)-4-iodobenzeneHCID 588241845-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

Product 1

HCID 588241974-(4'-Difluoromethoxy-biphenyl-4-ylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl esterYield 60.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

[1,1′-Bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (12.8 mg) was added to a degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester (151) (200 mg, 0.515 mmoles), 1-difluoromethoxy-4-iodo-benzene (153 mg, 0.568 mmoles) and 2M aqueous cesium carbonate (4.12 ml) in 1,4-dioxan (15 ml). The mixture was placed under an argon atmosphere and was heated at 100° C. for 20 hours. After cooling, the mixture was concentrated and the residue was partitioned between ethyl acetate and water, and the mixture adjusted to pH=2 with 1M aqueous hydrochloric acid. The organic phase was washed with brine and dried. After evaporation of the solvent, the residue was purified by flash chromatography, using heptane/ethyl acetate 9:1 v/v as eluent, to afford compound 152 (126 mg) as a white solid. LC/MS System A; Rt=4.17 mins.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. customdried
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3bd83c254f52442d9d4911b6cf0ccf25
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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