Trifluoroacetic acid → 1-(1,4-dioxaspiro[4.5]dec-8-yl)-6-(1H-indol-5-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole	HCID 2734772	—
Reactant	3-(6-chloro-1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane	HCID 60167522	—
Solvent	Ethanol	HCID 702	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	Acetonitrile	HCID 6342	—
Product	1-(1,4-dioxaspiro[4.5]dec-8-yl)-6-(1H-indol-5-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine	HCID 57424647	25%

Reaction Steps

6-Chloro-1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (0.20 g, 0.493 mmol) is treated with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (0.119 g, 0.74 mmol), aq. Na2CO3 (0.52 mL, 2M), and tetrakis triphenylphosphine palladium (20 mg) in 1:1 toluene:ethanol. The reaction mixture is heated in a microwave at 120 C for 60 min. Aq. workup followed by RP HPLC (H2O, CH3CN, TFA) gives the title compound as a white solid (60 mg). MS m/s=487.2 (M+H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08129371B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-9758579c52854634aa5fd1bba552e92b
Source note	uspto-grants-2012_03