Water → HCID 57624589, compound

HRID 1641565Notes

Reaction equation

HRID 1641565 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=2[F:22])=[CH:11][C:10]=1[Cl:23])(=[O:3])[CH3:2].[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([SH:40])=[CH:36][CH:35]=1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]([NH:29][C:30](=[O:32])[CH3:31])([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([S:40][C:37]3[CH:38]=[CH:39][C:34]([CH3:33])=[CH:35][CH:36]=3)=[CH:17][C:16]=2[F:22])=[CH:11][C:10]=1[Cl:23])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 78114-MethylbenzenethiolHCID 81531DiisopropylethylamineHCID 46203836HCID 46203836, compound

Product 1

HCID 57624589HCID 57624589, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[1,1-bis(acetoxymethyl)-3-(4′-bromo-3-chloro-2′-fluorobiphenyl-4-yl)propyl]acetamide (264 mg) of Reference Example 23, 4-methylbenzenethiol (62 mg), diisopropylethylamine (129 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (12.9 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (14.9 mg) in 1,4-dioxane (2 mL) was heated under reflux for 9 hr under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.24 g) as pale-yellow crystals.

Workup

  1. temperatureunder reflux for 9 hr under a nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-029eda17770a40fca6c9c2c60fe5c02c
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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