Triethylamine → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanesulfonyl chloride	HCID 31297	—
Reactant	3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90031238	—
Reactant	2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methane sulfonamide	HCID 131735668	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 118524053	71.42%

Reaction Steps

Using similar reaction conditions as described in step i of intermediate 17, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (product of step 1 of example 124) (75 mg, 0.123 mmol) was mesylated with methane sulfonyl chloride (17 mg, 0.148 mol) using triethylamine (35 μL, 0.247 mmol) in DCM (5 mL) to afford 60 mg (71.42% yield) of the titled compound. MS: m/z=685.1 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-80bf6d3823c347b192ba9c5580aeb929
Source note	uspto-grants-2016_05