Sodium Carbonate → tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90064814	—
Reactant	tert-butyl 4-(2-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 90064863	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate	HCID 118523958	83.4%

Reaction Steps

Using similar reaction conditions as described in step-i of example-1, 5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (intermediate 63B) (200 mg, 0.368 mmol) was coupled with tert-butyl 4-(2-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (intermediate 65E) (210 mg, 0.44 mmol) using Pd(PPh3)2Cl2 (13 mg, 0.018 mol) and sodium carbonate (117 mg, 11 mmol) in DME/water (10/1 mL) to afford 250 mg (83.3% yield) of the titled compound. MS: m/z=814.7 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-400963adbc74489d82e53904853cf156
Source note	uspto-grants-2016_05