Sodium Carbonate → 5-[2-Benzyloxy-4-(2-methylpropenyl)-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660772Notes

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.[CH3:24][C:25]([CH3:30])=[CH:26]B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:24]=[C:25]([CH3:30])[CH3:26])[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: 12 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (150 mg, 0.338 mmol) and 2,2-dimethylethenylboronic acid (67 mg, 0.670 mmol), resin-bound PPh3Pd (519 mg, 0.069 mmol) and Na2CO3 (0.338 mL, 2M) in DME (3 mL) is heated in a microwave apparatus at 12° C. for 20 min. The mixture is filtered through Celite, washed with MeCN and concentrated. The residue is purified by reverse phase chromatography using a gradient of 10-60% EtOH/H2O as eluent to afford the title compound: (M−1)−=371.

Workup

filtrationThe mixture is filtered through Celite
washwashed with MeCN
concentrationconcentrated
customThe residue is purified by reverse phase chromatography

Sources & evidence

ORD record: ord-6b4419203f4b49f8beb5573d66afca79
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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