Water → HCID 24852499, compound

HRID 1641561Notes

Reaction equation

HRID 1641561 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]3)=[CH:10][CH:9]=2)=[C:4]([F:28])[CH:3]=1.[CH3:29][C:30]1[CH:31]=[C:32]([SH:37])[CH:33]=[CH:34][C:35]=1[CH3:36].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>[CH3:29][C:30]1[CH:31]=[C:32]([S:37][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]4([NH:24][C:25](=[O:27])[CH3:26])[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]4)=[CH:10][CH:9]=3)=[C:4]([F:28])[CH:3]=2)[CH:33]=[CH:34][C:35]=1[CH3:36]

Participants

8

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 877993,4-Xylenethiol2×HCID 46203835HCID 46203835, compound

Product 1

HCID 24852499HCID 24852499, compoundYield 120.4%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Catalyst2×HCID 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)Catalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-{5-[2-(4′-bromo-2′-fluorobiphenyl-4-yl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (170 mg) of Reference Example 10, 3,4-dimethylbenzenethiol (52 mg), diisopropylethylamine (98 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (9.8 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (11.2 mg) in 1,4-dioxane (1.5 mL) was heated under reflux for 9 hr under a nitrogen atmosphere. 3,4-Dimethylbenzenethiol (10 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (3.9 mg) and Xantphos (4.4 mg) were added to the reaction mixture, and the mixture was further heated under reflux for 9 hr. 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 (0.23 g) as pale-yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-c44ff501a7814d6ea369457a43dc7232
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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