1,4-Dioxane → HCID 56651011, compound

HRID 1191310Notes

Reaction equation

HRID 1191310 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=[CH:15][CH:16]=3)[NH:11][C:10](=[O:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.CC(C)([O-])C.[Na+].C(=[NH:48])(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[NH2:48][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=[CH:15][CH:16]=3)[NH:11][C:10](=[O:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 312751,4-DioxaneHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86690450HCID 86690450, compound

Product 1

HCID 56651011HCID 56651011, compoundYield 25%

Procedure

The mixture of 4-(3-bromophenyl)-1H-benzo[h]quinazolin-2-one (950 mg, 2.71 mmol), 1,4-dioxane (95 mg, 1.08 mmol), sodium tert-butoxide (650 mg, 6.76 mmol), benzophenone imine (681 μL, 4.06 mmol), and (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (101 mg, 0.16 mmol) was heated under reflux for 16 hours under N2 atmosphere. The solvent was removed under reduced pressure. To the residue was added methanol (50 mL) and 2M hydrochloride (50 mL), and stirred at room temperature for 16 hours. The reaction mixture was filtered to give the titled compound as a yellow solid (191 mg, yield 25%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours under N2 atmosphere
  3. customThe solvent was removed under reduced pressure
  4. additionTo the residue was added methanol (50 mL) and 2M hydrochloride (50 mL)
  5. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-dceedefb1dfa4fcd8594b85877816381
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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