Water → HCID 69000493, compound

HRID 1821409Notes

Reaction equation

HRID 1821409 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=O)=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH2:35][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:27]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:35]/[C:28]3[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:26][N:27]=3)=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71627659HCID 71627659, compoundHCID 178419401HCID 178419401, compound

Product 1

HCID 69000493HCID 69000493, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(4-formyl-3-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 3.0 mmol) obtained in Step 1 in methanol (10 mL) was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.99 g, 3.0 mmol) and potassium carbonate (0.82 g, 5.9 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate) to obtain (E)-4-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}piperazine-1-carboxylic acid tert-butyl ester (0.22 g, 16%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate)

Sources & evidence

ORD record
ord-ce110fcfe5b9445da888aa32e3f68fbc
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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