1H-Indazole → HCID 66716790, compound

HRID 1184472Notes

Reaction equation

HRID 1184472 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N:13]1[N:14]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=2)[CH:15]=[C:16]2[C:21]=1[CH:20]=[CH:19][CH:18]=[CH:17]2

Participants

6

Reactant 3

HCID 92211H-IndazoleHCID 11430Potassium CarbonateHCID 24141064-(chloromethyl)-2-nitrophenol

Product 1

HCID 66716790HCID 66716790, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

In a 100 mL round-bottomed flask was added 4-(chloromethyl)-2-nitrophenol (1.0 g, 5.33 mmol), 1H-indazole (0.630 g, 5.33 mmol), and potassium carbonate (0.884 g, 6.40 mmol) in DMF (26.7 mL). The mixture was stirred at 23° C. for 18 h. The reaction was diluted with water (100 mL) and the resulting solid was isolated by filtration, washed with water, and dried in vacuo. The crude solid was purified via ISCO flash chromatography (0-75% EtOAc in hexanes; 40 g column) to give the title compound as a yellow solid (341 mg, 24% yield): 1H NMR (DMSO-d6, 400 MHz): δ=8.50 (d, J=1.0 Hz, 1H), 7.82 (d, J=2.0 Hz, 1H), 7.68-7.72 (m, 1H), 7.56-7.61 (m, 1H), 7.48 (dd, J=8.6, 2.3 Hz, 1H), 7.10 (dd, J=8.5, 7.2 Hz, 2H), 7.00-7.06 (m, 1H), 5.62 ppm (s, 2H). ESI-MS: m/z 270.2 (M+H)+.

Workup

  1. customthe resulting solid was isolated by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customThe crude solid was purified via ISCO flash chromatography (0-75% EtOAc in hexanes; 40 g column)

Sources & evidence

ORD record
ord-1345cf52cade48e79cbf12df4848640b
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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