1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 117677846, compound

HRID 1507481Notes

Reaction equation

HRID 1507481 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[C@@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]3[C@@H:11]([CH2:19][OH:20])[CH2:10]2)[C:5]([C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[C:4]([O:30][CH3:31])[N:3]=1.Br[C:33]1[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]([CH3:40])[CH:34]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]C1C=CC=CC=1.[Na+]>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.[Pd].[Pd]>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[C:5]1[C:6]([NH:8][C@H:9]2[C@@H:13]3[O:14][C:15]([CH3:17])([CH3:18])[O:16][C@@H:12]3[C@@H:11]([CH2:19][OH:20])[CH2:10]2)=[N:7][C:2]([NH:1][C:33]2[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]([CH3:40])[CH:34]=2)=[N:3][C:4]=1[O:30][CH3:31]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 130817354-Bromo-2,6-dimethylpyridineHCID 117677449HCID 117677449, compound

Product 1

HCID 117677846HCID 117677846, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Compound 10 (0.10 g, 0.225 mmol), 4-bromo-2,6-dimethylpyridine (0.108 g, 0.676 mmol), Xantphos (0.078 g, 0.135 mmol), sodium phenoxide (0.044 g, 0.383 mmol) and Pd2(dba)3 (0.041 g, 0.045 mmol) in dioxane (3.0 ml) were degassed and heated under nitrogen to reflux for 18 h. The reaction was cooled to room temperature and concentrated. The residue was then purified by column chromatrography on silica gel (MeOH/DCM) to give the title compound. LCMS 1.86 min, 549 (M+H)

Workup

  1. customwere degassed
  2. temperatureheated under nitrogen
  3. temperatureto reflux for 18 h
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatrography on silica gel (MeOH/DCM)

Sources & evidence

ORD record
ord-cdbfa37ee6fa4cccb0b8c21b572810dd
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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