Iodobenzene → 4-methoxy-N-phenylbenzo[d]thiazol-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Iodobenzene	HCID 11575	—
Reactant	4-Methoxy-2-aminobenzothiazole	HCID 21622	—
Reagent	Sodium t-butoxide	HCID 23676156	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-methoxy-N-phenylbenzo[d]thiazol-2-amine	HCID 7086338	15.22%

Reaction Conditions

Temperature	90 °C

Reaction Steps

4-methoxybenzo[d]thiazol-2-amine (0.216 g, 1.20 mmol), iodobenzene (0.112 mL, 1.00 mmol), XANTPHOS (0.058 g, 0.10 mmol), Pd2(dba)3 (0.027 g, 0.03 mmol) and SODIUM TERT-BUTOXIDE (0.192 g, 2.00 mmol) placed in a sealed reaction via under an atmosphere of nitrogen and heated at 90ºC for 1 hour. LC/MS indicated mainly product, little SM. Cooled, diluted DCM and washed with water and brine. Org phase dried/MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, eluting with dichloromethane. Pure fractions were evaporated to dryness to afford 4-methoxy-N- phenylbenzo[d]thiazol-2-amine (0.039 g, 15.22 %) as an colorless solid. EN01327-44-1 (0.039 g, 0.15 mmol, 15.22 %) Not sure why yield so low, crude lc/ms looked fine. Reaction left for several days before working up.

Provenance & Evidence

Source dataset	750 AstraZeneca ELN dataset
ORD ID	ord-0eb7fc5c164b43bc9a05a46e98a37b12
Source note	750 AstraZeneca ELN dataset