Sodium Carbonate → tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 69132726	—
Reactant	tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperidine-1-carboxylate	HCID 90031040	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperidine-1-carboxylate	HCID 118524082	71.9%

Reaction Steps

Using similar reaction conditions as described in step-i of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperidine-1-carboxylate (intermediate 67A) (260 mg, 0.378 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (172 mg, 0.567 mmol) using Pd(dppf)Cl2 (14 mg, 0.018 mol) and sodium carbonate (121 mg, 1.134 mmol) in toluene/ethanol/water (6/2/1 ml) to afford 200 mg (71.9% yield) of the titled compound after column purification using 2% methanol in DCM as eluent. MS: m/z=736.4 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-bf487faab7cc45e182bd4a58c643cda3
Source note	uspto-grants-2016_05