Triphenylphosphine → HCID 57764525, compound

HRID 713727Notes

Reaction equation

HRID 713727 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[C:9](Br)[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:4]=2[N:5]=[N:6][N:7]=1.[CH:21]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[Al](C)C>C[Si](C)(C)N[Si](C)(C)C.C1COCC1.Cl[Pd]Cl>[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([CH3:21])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:4]=2[N:5]=[N:6][N:7]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 16682925TrimethylaluminumHCID 57764505HCID 57764505, compound

Product 1

HCID 57764525HCID 57764525, compoundYield 310%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

The compound from Step A (112 mg, 0.3 mmol) was heated at reflux in hexamethyldisilazane (15 mL) for 16 hours. The mixture was evaporated to dryness to give a syrup which was dissolved in dry THF (12 mL). PPh3 (10 mg; 0.04 mmol), PdCl2 (3.5 mg; 0.02 mmol) and AlMe3 (100 μl; 0.94 mmol) were added. The mixture was reflux for 5 hours. The mixture was evaporated to dryness. The crude product was dissolved in methanol (30 mL) in the presence of ammonium chloride. The mixture was evaporated to dryness and the residue was purified on silica gel reverse-phase (C18) using water/acetonitrile (from 9/1 to 6/4) as eluant to give the title compound (35 mg) as a yellow powder.

Workup

  1. customThe mixture was evaporated to dryness
  2. customto give a syrup which
  3. temperatureThe mixture was reflux for 5 hours
  4. customThe mixture was evaporated to dryness
  5. dissolutionThe crude product was dissolved in methanol (30 mL) in the presence of ammonium chloride
  6. customThe mixture was evaporated to dryness
  7. customthe residue was purified on silica gel reverse-phase (C18)

Sources & evidence

ORD record
ord-6621c3c1daa24d7f9f1bf50a96529aa4
Source dataset
uspto-grants-2015_11
Patent number
US09186369B2

Reaction notes

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