5-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one → HCID 68843474, compound

HRID 660819Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([Cu])#[N:25]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[N:16]1[CH2:17][C:18](=[O:23])[NH:19][S:20]1(=[O:22])=[O:21])[C:24]#[N:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (108.4 mg, 0.243 mmol) in DMF (2 mL) is added KHCO3 (0.488 mL, 0.5M aqueous solution), CuCN (19 mg, 0.212 mmol) and resin-bound PPh3Pd (10 mol %) in DMF (2 mL) and the mixture is heated in a microwave apparatus at 110° C. for 20 min. The solvent is removed under reduced pressure and the residue purified by reverse phase MPLC to give the title compound.

Workup

customThe solvent is removed under reduced pressure
customthe residue purified by reverse phase MPLC

Sources & evidence

ORD record: ord-9f1fc64f40224420a4ffdfedd16b9b12
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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