Cesium carbonate → 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Benzenesulfonamide, N,4-dimethyl-	HCID 12543	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester	HCID 68637361	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester	HCID 68637032	37.5%

Reaction Conditions

Temperature	130 °C

Reaction Steps

Under argon, 340 mg 6-Bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester (see example 132), 157 mg N-methyl-para-toluenesulfonamide, 322 mg cesium carbonate, 32 mg Pd2(dba)3, and 30 mg xantphos are dissolved in 6.8 mL toluene. Argon is bubbled through the solution for 5 minutes. The reaction mixture is heated to 130° C. for 1 hour in a microwave oven. Then the reaction mixture is diluted with EtOAc and washed with water. The organic phase is dried (MgSO4) and the solvent removed in vacuo. Purification by HPLC affords 155 mg (37%) 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07709466B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-fa6775ac077c4d31bbcfeeb15f0bd174
Source note	uspto-grants-2010_05