Water → HCID 69002133, compound

HRID 1821387Notes

Reaction equation

HRID 1821387 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.C(N(CC)CC)C.C[O:27][C:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[C:30]=1[CH2:38]Br.O>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH2:38][C:30]3[C:29](=[CH:34][CH:33]=[CH:32][C:31]=3[N+:35]([O-:37])=[O:36])[C:28]2=[O:27])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 69001756HCID 69001756, compound

Product 1

HCID 69002133HCID 69002133, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Compound 2 (70 mg, 0.26 mmol) in DMF (1.4 mL), triethylamine (91 μL, 0.68 mmol) and 2-bromomethyl-3-nitrobenzoic acid methyl ester (79 mg, 0.29 mmol) were added, followed by stirring at 80° C. for 7.0 hours under nitrogen atomosphere. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) to obtain (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-4-nitro-2,3-dihydroisoindol-1-one (61 mg, 60%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)

Sources & evidence

ORD record
ord-b5cf6efbf4234c7eb48a9f63677fb484
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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