Potassium Carbonate → HCID 86690717, compound

HRID 1473889Notes

Reaction equation

HRID 1473889 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N:18]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:4]([C:3]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:2]=1[O:1][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N:18]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 86690716HCID 86690716, compound

Product 1

HCID 86690717HCID 86690717, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-hydroxy-5-methoxybenzaldehyde (46 mg, 0.3 mmol), tert-butyl 4-(chloromethyl)-1H-indazole-1-carboxylate (80 mg, 0.3 mmol), and K2CO3 (166 mg, 1.2 mmol) in DMF (1.0 mL) was heated at 80° C. for 2 h. The mixture was filtered and the solid was washed with DCM. The filtrate was concentrated and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give tert-butyl 4-((2-formyl-4-methoxyphenoxy)methyl)-1H-indazole-1-carboxylate (88 mg, 77%) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified on silica gel using
  5. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-91605ce6b4f64744b47b91e0e56b84c4
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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