Cesium carbonate → 5-(4-Benzofuran-3-yl-2-benzyloxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660722Notes

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.CC1(C)C(C)(C)OB([C:32]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[O:34][CH:33]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:34]1[C:33]2=[CH:32][CH:36]=[CH:37][C:38]2=[CH:39][C:40]([C:14]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([N:16]3[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]3)[CH:11]=[CH:12][CH:13]=2)=[CH:35]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (80 mg, 0.18 mmol), 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran (44 mg, 0.18 mmol), Cs2CO3 (235 mg, 0.72 mmol) and Pd(PPh3)4 (8 mg) in DMF (5 mL) is stirred at 80° C. for 7 h. The mixture is cooled to RT and is diluted with EtOAc, washed with water and bride and dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound.

Workup

temperatureThe mixture is cooled to RT
washwashed with water and bride
dry with materialdried over magnesium sulfate
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-48738fbc4cc84c85900d3214c7015b0b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

Loading…