Sodium Carbonate → 5-[2-Benzyloxy-4-(1-propyl-1H-pyrazol-4-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-4-one

HRID 660738Notes

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)[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1)[CH2:25][CH3:26].C([O-])([O-])=[O:42].[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:30]2[CH:29]=[N:28][N:27]([CH2:24][CH2:25][CH3:26])[CH:31]=2)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][CH2:18][C:17]1=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (100 mg, 0.225 mmol), 1-propyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (106 mg, 0.45 mmol), resin-bound PPh3Pd (177 mg, loading 0.13 mmol/g) and aqueous Na2CO3 (0.45 mL of a 2M solution) in DME (3 mL) is heated in a microwave apparatus at 110° C. for 10 min. The mixture is filtered and the solvent removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

filtrationThe mixture is filtered
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-c02dc77bd56e4e99ad705bb83c4cbc21
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

Loading…