1,4-Dioxane → HCID 69659142, compound

HRID 1829065Notes

Reaction equation

HRID 1829065 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]([CH2:21][C:22]([OH:24])=[O:23])[O:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.O1CCOC[CH2:26]1>CO>[CH3:26][O:23][C:22](=[O:24])[CH2:21][CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[O:13]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 69659264HCID 69659264, compound

Product 1

HCID 69659142HCID 69659142, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of [3-(6-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (300 mg, 0.922 mmol) in a mixture of dioxane (15 ml) and MeOH (7 ml) was added 2.0M (trimethylsilyl)diazomethane/Hexanes (507 μl) and the resultant solution was stirred for 15 minutes at room temperature. The solvent was rotary evaporated and the residue was partitioned between EtOAc and saturated NaHCO3. The organic layer (combined a EtOAc solution from a previous 100 mg (0.307 mmol) scale test reaction) was then washed with dilute HCl aqueous solution, water, brine, dried with anhydrous Na2SO4, and rotary evaporated to a yellow solid. The solid was triturated with 30% EtOAc in hexane to yield [3-(6-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid methyl ester as a bright yellow solid (388 mg, 93%).

Workup

  1. customThe solvent was rotary evaporated
  2. customthe residue was partitioned between EtOAc and saturated NaHCO3
  3. customfrom a previous 100 mg (0.307 mmol) scale test reaction)
  4. washwas then washed with dilute HCl aqueous solution, water, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customrotary evaporated to a yellow solid
  7. customThe solid was triturated with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-a06965c019364118b15a6e2b45156339
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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