Iodobenzene → HCID 44180967, compound

HRID 1042039Notes

Reaction equation

HRID 1042039 reaction equation
[Br:1][C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.[C:18]1(I)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+]>[N+]([O-])([O-])=O.[Ag+].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.CS(C)=O>[Br:1][C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 11575IodobenzeneHCID 522689Potassium FluorideHCID 441811783-Bromo-5-(morpholin-4-yl)-7H-thieno[3,2-b]pyran-7-one

Product 1

HCID 44180967HCID 44180967, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (50 mg, 158 μmol), phenyl iodide (27 mg, 132 μmol), potassium fluoride (11.5 mg, 198 μmol), silver nitrate (34 mg, 198 μmol), anhydrous dimethyl sulfoxide (1 mL), and dichlorobis(triphenylphosphine)palladium (II) (4.6 mg, 6.6 mop. The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated under microwave irradiation to 120° C. for 15 minutes to give 3-bromo-5-morpholino-2-phenyl-7H-thieno[3,2-b]pyran-7-one (76).

Workup

  1. additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
  2. customThe reaction mixture was sealed

Sources & evidence

ORD record
ord-62e4db09ba1d459c9d01bda7014e23e9
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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