Triphenylphosphine → HCID 86663078, compound

HRID 2201013Notes

Reaction equation

HRID 2201013 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[C:33]([NH2:35])[C:32](I)=[CH:31][N:30]=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:28][C:29]1[CH:34]=[C:33]([NH2:35])[C:32]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[O:38][CH3:37])=[CH:31][N:30]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acidHCID 454803662-Chloro-5-iodopyridin-4-amine

Product 1

HCID 86663078HCID 86663078, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
75 °C

Procedure

Potassiumphosphate (18.28 g, 79 mmol), triphenyl phosphine (1.04 g, 3.97 mmol), 2-chloro-5-iodo-4-aminopyridine (10.1 g, 39. mmol), 2-methoxybenzeneboronic acid (8.44 g, 55.57 mmol) and palladium acetate (0.45 g, 1.98 mmol) were sequentially added to degassed acetonitrile (300 mL) and water (100 mL) under nitrogen. The reaction mixture was heated at 75° C. for overnight, then cooled to room temperature. The organic layer was separated and aqueous layer and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and performed column chromatography using hexanes and ethyl acetate as eluent. 7.5 g of title compound was isolated.

Workup

  1. customto degassed acetonitrile (300 mL) and water (100 mL) under nitrogen
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. extractionaqueous layer and was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f08475a938642769fb31de21fbb3332
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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