Sodium Carbonate → 1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	6-Bromo-2,3-dihydro-1,2-benzothiazole-1,1,3-trione	HCID 10540996	—
Reactant	1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide	HCID 59206473	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide	HCID 25152661	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (46 mg, 0.10 mmol), 6-bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (26 mg, 0.10 mmol), Pd(dppf)Cl2 (4.0 mg, 0.0050 mmol), 2M Na2CO3 (150 μL, 0.30 mmol), and DMF (1 mL) were combined and heated at 120° C. in the microwave for 10 min. The mixture was filtered and purified by reverse phase preparatory HPLC to give 1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide. ESI-MS m/z calc. 512.5, found 513.5 (M+1)+. Retention time 1.93 minutes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08039491B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-d46812d6f281443e99a48a0a8da7c3b3
Source note	uspto-grants-2011_10