Potassium Phosphate, Tribasic → HCID 67079577, compound

HRID 453394Notes

Reaction equation

HRID 453394 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:13]=[C:12]([C:14]#[N:15])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1Br.[F:18][C:19]1[CH:24]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=1[NH2:29].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].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>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[C:5]([NH:29][C:20]2[CH:21]=[CH:22][C:23]([Si:25]([CH3:27])([CH3:26])[CH3:28])=[CH:24][C:19]=2[F:18])[C:4]([C:3]([O:2][CH3:1])=[O:17])=[CH:13][C:12]=1[C:14]#[N:15]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 595965992-Fluoro-4-(trimethylsilyl)anilineHCID 67079365HCID 67079365, compound

Product 1

HCID 67079577HCID 67079577, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-cyano-terephthalic acid dimethyl ester (620 mg, 2.1 mmol), 2-fluoro-4-trimethylsilanyl-phenylamine (419 mg, 2.3 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (62 mg, 0.10 mmol), potassium phosphate (486 mg, 2.30 mmol) and tris(dibenzylideneacetone)dipalladium (0) (29 mg, 0.05 mmol) were suspended in dioxane (20 ml) and the resultant mixture purged with argon. The reaction mixture was heated at reflux for 16 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 ml) and the resultant mixture extracted with ethyl acetate (3×20 mL). The combined organic fractions were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-40% ethyl acetate in cyclohexane) to yield the title compound as a brown solid (0.5 g, 60%). LCMS (Method B): RT=4.74 min, M+H+=401.

Workup

  1. customthe resultant mixture purged with argon
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 16 hours
  4. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 ml)
  5. extractionthe resultant mixture extracted with ethyl acetate (3×20 mL)
  6. washThe combined organic fractions were washed with brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d1000c3f1ca458ea1e21c8eb808add7
Source dataset
uspto-grants-2013_07
Patent number
US08492427B2

Reaction notes

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