4-(3-(6-Ethynylnaphthalen-2-yloxy)propyl)morpholine → methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-((6-(3-morpholinopropoxy)naphthalen-2-yl)ethynyl)thiazole-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	4-(3-(6-Ethynylnaphthalen-2-yloxy)propyl)morpholine	HCID 59447602	—
Reactant	methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-iodothiazole-4-carboxylate	HCID 59447651	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Product	methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-((6-(3-morpholinopropoxy)naphthalen-2-yl)ethynyl)thiazole-4-carboxylate	HCID 59447598	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a mixture of compound 47D (200 mg, 0.283 mmol), compound 110C, (PPh3)2PdCl2 (49.7 mg, 0.071 mmol), TEA (0.394 ml, 2.83 mmol) in DMF (5 ml) was added copper (I) iodide (5.40 mg, 0.028 mmol). The resulting mixture was heated at 120° C. in oil bath for 5 h. The reaction mixture was concentrated and purified by RP HPLC, eluting with 10-95% acetonitrile in 0.1% TFA water over 70 min to provide compound 110D: LCMS (APCI) 875 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08232273B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-1325b3054fe6426da36c4f83b5f3611d
Source note	uspto-grants-2012_07