1,4-Dioxane → Isohexane ethyl acetate

HRID 2306714Notes

Reaction equation

HRID 2306714 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=CC(NC2C3C(=CC=C(Br)C=3)N=CN=2)=CC=1)[C:2]1[CH:7]=C[CH:5]=[CH:4][CH:3]=1.CN1C([Sn](CCCC)(CCCC)CCCC)=CN=N1.[O:46]1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]([O:8][CH2:1][CH3:2])(=[O:46])[CH3:14].[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 1569266(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amineHCID 226098261-methyl-5-(tributylstannyl)-1H-1,2,3-triazole

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (250 mg, 0.62 mmol), 1-methyl-5-(tributylstannyl)-1,2,3-triazole (300 mg, 0.81 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (10 ml) and heated at reflux under nitrogen for 48 hr. The solvent was removed from the cooled reaction under vacuum, and the residue was triturated with iso-hexane. The resulting material was dissolved in ethyl acetate, filtered and the filtrate evaporated to dryness. Trituration with ethyl acetate/iso-hexane gave the product (115 mg, 45%) as a beige solid; δH [2H6]-DMSO 9.90 (1H, b, NH), 8.76 (1H, s, 5-H), 8.61 (1H, s, 2-H), 8.10 (2H, m, 7-H, triazole-H), 7.92 (1H, d, 8-H), 7.70 (2H, d, 2′-H, 6′-H), 7.58-7.38 (5H, m, 5×Ph-H), 7.12 (2H, d, 3′-H, 5′-H), 5.19 (2H, s, CH2), 4.22 (3H, s, CH3); m/z 409 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 48 hr
  3. customThe solvent was removed from the cooled reaction under vacuum
  4. customthe residue was triturated with iso-hexane
  5. dissolutionThe resulting material was dissolved in ethyl acetate
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-9d32a2ab53ac4cb9ade4cbe54ea047f9
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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