Lithium Chloride → (1R,2R)-2-methyl-cyclopropane carboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide

https://huagongshe.com/reaction/2079746

Participants

Role	Name	HCID	Charge
Reactant	Lithium Chloride	HCID 433294	—
Reactant	2-Methyl-5-(trimethylstannyl)-2H-indazole	HCID 66838439	—
Reactant	(R,R)-N-[3,4-dibromoisothiazol-5-yl]-2-methylcyclopropanecarboxamide	HCID 67103560	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Methylpentane	HCID 7892	—
Product	(1R,2R)-2-methyl-cyclopropane carboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide	HCID 67103132	43%

Reaction Conditions

Temperature	105 °C

Reaction Steps

Charge a round bottom flask with (1R,2R)-2-methyl-cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amide (2.55; g, 7.49; mmol), 2-methyl-5-trimethylstannanyl-2H-indazole (2.21; g, 7.49; mmol) and lithium chloride (0.95; g, 22.48; mmol) in 1,4-dioxane (19.2; mL). Purge with nitrogen for 20; min, add tetrakis(triphenylphosphine) palladium (1.31; g, 1.12; mmol) and heat at 105° C. for 48; h. Directly load reaction mixture onto a silica gel column and purify by gradient eluting from 0:100; to 100:0; ethyl acetate:iso-hexane to give the title compound (1.25; g, 43%). MS (m/z): 391, 393; (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932274B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-0eee5c15b07b4e6092a4e2a81bdacc08
Source note	uspto-grants-2011_04