1H-Indazole → HCID 67282655, compound

HRID 1616172Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.I[C:11]1[CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=[CH:15][CH:16]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>O>[N:1]1([C:11]2[CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 135 °C

Procedure

To a round bottom flask was added 1H-indazole (0.47 g, 4.0 mmol), (3-iodophenyl)methanol (1.4 g, 6.0 mmol), ferric chloride (0.13 g, 0.8 mmol), and tri-potassium phosphate monohydrate (1.84 g, 8.0 mmol). Degassed water (2 mL) was then added followed by (1R,2R)—N,N′-dimethylcyclohexane-1,2-diamine (0.25 mL, 1.6 mmol). The reaction mixture was then heated to 135° C. and stirred overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford [3-(1H-indazol-1-yl)phenyl]methanol (0.67 g, 74%). LC-MS: (FA) ES+ 225.

Workup

temperatureThe mixture was cooled to rt
extractionextracted with EtOAc (2×)
washThe combined organic phases were then washed with water, and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-93bfaf72406b4c4da9e3ec8ee7f8e373
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

Loading…