Ethyl Acetate → 5-(2-Benzyloxy-4-furan-3-yl-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660719Notes

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.[O:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>C(COC)OC.O.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:26]2[CH:27]=[CH:28][O:24][CH:25]=2)[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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (163 mg, 0.37 mmol), furan-3-boronic acid (62 mg, 0.550 mmol), potassium phosphate (235 mg, 1.1 mmol), and palladium dppf (9 mg, 0.011 mmol) in 6 mL of glyme/water (9:1) is heated in a microwave apparatus at 120° C. for 25 min. The mixture is poured into EtOAc and extracted with 1N HCl and saturated NaCl. The organic phase is dried and the solvent removed is under reduced pressure to leave a crude semi-solid that is chromatographed on a C18 column using a gradient of 0-60% water/acetonitrile as eluent. The aqueous is lyophilized to afford the title compound as a hygroscopic solid: 1H NMR (DMSOd6) δ 8.1 (s, 1H), 7.7 (s, 1H), 7.5 (d, J=8.3 Hz, 1H), 7.4 (m, 6H), 7.1 (dd, J=8.3, 1.8 Hz, 1H), 6.9 (s, 1H), 5.2 (s, 2H), 4.0 (s, 2H); (M−1)−=383.

Workup

extractionextracted with 1N HCl and saturated NaCl
customThe organic phase is dried
customthe solvent removed
customto leave a crude semi-solid
customthat is chromatographed on a C18 column

Sources & evidence

ORD record: ord-9c76914ecca24608b3fae6e91b785ddb
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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