N,N-Dimethylglycine → 3-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

https://huagongshe.com/reaction/1991102

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylglycine	HCID 673	—
Reactant	Thiophenol	HCID 7969	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	5-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine	HCID 59128688	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine	HCID 59186587	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 22 (50 mg, 0.079 mmol), benzenethiol (13.0 mg, 0.118 mmol), copper (I) iodide (3.0 mg, 0.016 mmol), N,N-dimethylglycine (1.62 mg, 0.016 mmol) and potassium phosphate (41.8 mg, 0.197 mmol) in DMF (0.5 mL) were heated at 120° C. for 69 h. The reaction mixture was cooled and partitioned between AcOEt/brine, the layers separated and the aqueous phase extracted with more AcOEt (2×). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude residue containing 23 was used for the subsequent deprotection step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07645769B2
Source dataset	uspto-grants-2010_01
ORD ID	ord-5ecd8133a2d744029393622811a89cea
Source note	uspto-grants-2010_01