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

HRID 475122Notes

Reaction equation

I[C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:27]B1OB(C)OB(C)O1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:27][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

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]+.

Workup

filtrationThe reaction mixture was filtered
additionthe filtrate diluted with H2O
extractionextracted with EtOAc
dry with materialThe combined extracts extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

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

Reaction notes

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