[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([I:19])=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:27][C:28](Cl)=[O:29]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[I:19][C:7]1[C:6](=[O:20])[C:5]2[C:10](=[C:11]3[C:2](=[CH:3][CH:4]=2)[NH:1][C:28](=[O:29])[CH2:27][O:12]3)[O:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
To a solution of 7-amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one (150 mg, 0.40 mmol), benzyltriethylammonium chloride (91 mg, 0.40 mmol) and NaHCO3 (168 mg, 2 mmol) in CHCl3 (5 mL) at 0° C. was added a solution of chloroacetyl chloride (35 μL, 0.44 mmol) in CHCl3 (1 mL) dropwise over 30 mins. The reaction mixture was stirred at 0° C. for 2 hours before heating at 50° C. for 18 hours. The resultant mixture was cooled to RT and was partitioned between DCM and water. The aqueous phase was filtered and the solid collected and azeotroped with methanol to give the title compound as a beige solid (167 mg, 99%). LCMS (Method G): RT=3.18 min, [M+H]+=420.
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