1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 57551215, compound

HRID 1644647Notes

Reaction equation

HRID 1644647 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[C:59]([N:63]1[C:67]([NH2:68])=[CH:66][C:65]([C:69]([CH3:72])([CH3:71])[CH3:70])=[N:64]1)([CH3:62])([CH3:61])[CH3:60].CC(C)([O-])C.[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]>[C:59]([N:63]1[C:67]([NH:68][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:66][C:65]([C:69]([CH3:72])([CH3:71])[CH3:70])=[N:64]1)([CH3:62])([CH3:61])[CH3:60]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 23676156Sodium t-butoxideHCID 433814531,3-Di-tert-butyl-1H-pyrazol-5-amine

Product 1

HCID 57551215HCID 57551215, compoundYield 24.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-iodo-N-thiazol-2-yl-benzenesulfonamide (100 mg, 0.3 mmol, 1.0 equiv), tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol, 0.04 equiv), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19 mg, 0.033 mmol, 0.12 equiv) and 2,5-di-tert-butyl-2H-pyrazole-3-ylamine (70 mg, 0.36 mmol, 1.2 equiv) in 4.0 mL of anhydrous 1,4-dioxane was added sodium tert-butoxide (100 mg, 0.90 mmol, 3.0 equiv). The vial was capped, and the reaction mixture was heated 30 min at 150° C. in the microwave. The crude reaction mixture was filtered through celite then concentrated in vacuo. The residue was dissolved in 0.5 mL of 1:1 dimethyl sulfoxide-acetonitrile then purified further via reverse phase HPLC. The appropriate fractions were lyophilized from water-acetonitrile to afford the product as an off-white solid (32 mg, 20%).

Workup

  1. customThe vial was capped
  2. customThe crude reaction mixture
  3. filtrationwas filtered through celite
  4. concentrationthen concentrated in vacuo
  5. dissolutionThe residue was dissolved in 0.5 mL of 1:1 dimethyl sulfoxide-acetonitrile
  6. customthen purified further via reverse phase HPLC

Sources & evidence

ORD record
ord-8c4ca9ce72fa4592a7254ef3874458df
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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