Water → methyl (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetate

HRID 1821433Notes

Reaction equation

HRID 1821433 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([O:15][CH3:16])[C:4]=1[N+:17]([O-:19])=[O:18])=O.[Br-].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:22]1.C(=O)([O-])[O-].[K+].[K+].O>CO.C(O)C>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](/[CH:30]=[CH:1]/[C:3]2[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([O:15][CH3:16])[C:4]=2[N+:17]([O-:19])=[O:18])=[N:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 86628221Methyl (4-formyl-2-methoxy-3-nitrophenoxy)acetateHCID 178419401HCID 178419401, compound

Product 1

HCID 86628222methyl (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetateYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Methyl (4-formyl-2-methoxy-3-nitrophenoxy)acetate (2.3 g, 8.5 mmol) obtained in Step 1, (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (4.4 g, 9.4 mmol) and potassium carbonate (2.4 g, 17 mmol) were dissolved in methanol (15 mL) and the solution was stirred at room temperature for 2.0 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was reslurried with ethanol to obtain methyl (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetate (2.8 g, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained crude product

Sources & evidence

ORD record
ord-8bbf427150d645cd9fbddb1162c4d88d
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…