Dichloromethane → Dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-(3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine	HCID 67256870	—
Reactant	(5-Bromothiazol-2-yl)dicyclopropylmethanol	HCID 67429273	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol	HCID 67258049	68.2%

Reaction Steps

A solution of the product of Step 2 (239 mg, 0.872 mmol), crude product of Step 3 (320 mg, ˜0.96 mmol), Pd(dppf)Cl2 (31.9 mg, 0.044 mmol) and Na2CO3 (aq) (2.0 M, 1.3 mL, 2.6 mmol) in DME (4.4 mL) was irradiated to 130° C. in the microwave for 35 minutes. The reaction mixture was filtered through a celite pad with dichloromethane and the filtrate was concentrated. The residue was purified twice by chromatography on silica gel (0-100% ethyl acetate in hexanes then 0-60% dichloromethane in ethyl acetate) to give the desired dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol (239 mg, 0.595 mmol, 68% yield) as a yellow solid. MS APCI: [M-OH]+ m/z 385.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08551984B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-f8db04de53c74a3f8d8c52f752683a10
Source note	uspto-grants-2013_10