Potassium Phosphate, Tribasic → 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Trimethylboroxine	HCID 574072	—
Reactant	3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile	HCID 71272550	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile	HCID 71272249	35.5%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (50 mg, 0.142 mmol), K3PO4 (61.34 mg, 0.284 mmol), Pd(dppf)Cl2 (10.3 mg, 0.0142 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (18 mg, 0.142 mmol) in DMF (0.5 mL) under nitrogen in a sealed vial was heated at 120° C. in a microwave oven for 100 minutes. The reaction mixture was filtered and the filtrate diluted with H2O and extracted with EtOAc. The combined extracts extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (12 mg, 35.5%). MS (ESI): m/z=242 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637537B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-1e47e1417ead45b1a9251378cb20aece
Source note	uspto-grants-2014_01