Triphenylphosphine → HCID 18374631, compound

HRID 2300049Notes

Reaction equation

HRID 2300049 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C1COCC1.C1(C)C=CC=CC=1.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[C:23]([CH2:34][C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)=[N:22][N:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Zn].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)Cl>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[C:23]([CH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)=[N:22][N:21]=[C:20]2[C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

8

Reactant 4

HCID 11776Triphenylphosphine3×HCID 764302-BromothiazoleHCID 18504793HCID 18504793, compoundHCID 22635083Tetrahydrofuran toluene

Product 1

HCID 18374631HCID 18374631, compoundYield 38.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 167845palladium(II) acetateCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

In anhydrous environment, bromothiazole (831 mg, 5.067 mmoles) and 2:1 THF/toluene (15 ml) were added dropwise to powder zinc (500 mg, 7.6 mmoles), with mild heating. The mixture was brought to reflux for 1.5 hours, then added with 1-chloro-6,7-dimethoxy4-pyridin-4-ylmethyl-phthalazine (800 mg, 2.53 mmoles), obtained as described in example 15, palladium acetate (28 mg) and triphenylphosphine (66 mg). The mixture was kept under reflux for 3 hours, then added with palladium acetate (56 mg) and triphenylphosphine (133 mg) and kept under reflux overnight. Further palladium acetate (56 mg) and triphenylphosphine (133 mg) were added and after 4 hours the mixture was poured into methylene chloride/30% aqueous ammonia. The phases were separated and the organic one was washed with water, dried and brought to dryness to give a crude which was chromatographed (eluent: methylene chloride/methanol 2.4%) to give 354 mg of the title compound (yield: 38.4%).

Workup

  1. temperatureto reflux for 1.5 hours
  2. customobtained
  3. temperatureunder reflux for 3 hours
  4. temperatureunder reflux overnight
  5. customThe phases were separated
  6. washthe organic one was washed with water
  7. customdried
  8. customto give a crude which
  9. customwas chromatographed (eluent: methylene chloride/methanol 2.4%)

Sources & evidence

ORD record
ord-252211f099754601937e676e5172e5b6
Source dataset
uspto-grants-2002_12
Patent number
US06498160B2

Reaction notes

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