1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 25056522, compound

HRID 1513045Notes

Reaction equation

HRID 1513045 reaction equation
C(O[C:6]([NH:8][C:9]1[C:10]([CH3:21])=[CH:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][C:14]=1I)=[O:7])(C)(C)C.[Cl:22][C:23]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([S:32][C:33]([CH3:41])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:34])=[CH:26][C:24]=1[NH2:25].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.CC(C)([O-])C.[Na+]>O1CCCC1.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.[Pd].[Pd].C(OCC)(=O)C>[Cl:22][C:23]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([S:32][C:33]([CH3:34])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH3:41])=[CH:26][C:24]=1[N:25]1[C:14]2=[N:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]([CH3:21])=[C:9]2[NH:8][C:6]1=[O:7]

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 59309664HCID 59309664, compoundHCID 59309943HCID 59309943, compound

Product 1

HCID 25056522HCID 25056522, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 5-(tert-butoxycarbonylamino)-6-iodo-4-methylpyridine-2-carboxylate (0.2 g), 2-chloro-4-methoxy-5-(1-methyl-1-phenylethylthio)aniline (0.15 g), tris(dibenzylideneacetone)dipalladium(0) (23 mg), 4,5-bis(diphenyl-phosphino)-9,9-dimethylxanthene (29 mg) and sodium tert-butoxide (66 mg) in tetrahydrofuran (4 mL) was heated at reflux under an argon atmosphere overnight. The reaction mixture was cooled to room temperature. To the reaction mixture was added ethyl acetate, and the insoluble material was removed by filtration. The filtrate was washed with 1 mol/L hydrochloric acid and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1−1/1) to give the title compound (90 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an argon atmosphere overnight
  3. customthe insoluble material was removed by filtration
  4. washThe filtrate was washed with 1 mol/L hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1−1/1)

Sources & evidence

ORD record
ord-649531426db94c1a99de899a167e6301
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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