Potassium Carbonate → HCID 71621141, compound

HRID 1473888Notes

Reaction equation

HRID 1473888 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[CH3:23].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[N:17][N:18]3[CH3:23])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 866907154-(Chloromethyl)-1-methyl-1H-indazole

Product 1

HCID 71621141HCID 71621141, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-hydroxy-5-methoxybenzaldehyde (170 mg, 1.12 mmol), 4-(chloromethyl)-1-methyl-1H-indazole (1.12 mmol), and K2CO3 (618 mg, 4.48 mmol) was reflux in CH3CN (20 mL) 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 MeOH as eluent to give 5-methoxy-2-((1-methyl-1H-indazol-4-yl)methoxy)benzaldehyde (215 mg, 81% for three steps) as a white solid. 1H NMR (400 MHz; DMSO) δ=10.39 (s, 1H), 8.20 (d, 1H), 7.63 (d, 1H) 7.36-7.64 (m, 2H), 7.23-7.29 (m, 2H), 7.18 (d, 1H), 5.58 (s, 2H), 4.06 (s, 3H), 3.34 (s, 3H). LRMS (M+H+) m/z 297.1.

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 MeOH as eluent

Sources & evidence

ORD record
ord-1149250aa3644a6e963713b7f1ff0bd4
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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