Water → (E)-3-{2-[5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrophenyl]vinyl}-1H-indazole

HRID 1821426Notes

Reaction equation

HRID 1821426 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=O.[Br-].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH2:34][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:26]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][O:2][C:3]1[C:4]([O:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7](/[CH:8]=[CH:34]/[C:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][N:26]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282185-Methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 68998380(E)-3-{2-[5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrophenyl]vinyl}-1H-indazoleYield 112.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-methoxy-4-[3-(morpholin-4-yl) propyloxy]-2-nitrobenzaldehyde (0.26 g, 0.79 mmol) obtained in Step 1 in methanol (8.0 mL) was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.73 g, 1.5 mmol) and potassium carbonate (0.34 g, 2.8 mmol), followed by stirring at room temperature for 3.5 hours. The reaction mixture was added with water and the precipitated solid was triturated in methanol to obtain (E)-3-{2-[5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrophenyl]vinyl}-1H-indazole (0.39 g, 100%).

Workup

  1. customthe precipitated solid was triturated in methanol

Sources & evidence

ORD record
ord-a83b383d9a544ae4bb24ce7cd31ff241
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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