Tetrahydrofuran → HCID 57608191, compound

HRID 1171226Notes

Reaction equation

HRID 1171226 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH2:16][N:17]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:12][C:10]=3[CH:11]=2)=[CH:4][CH:3]=1.O1CCCC1.O.NN.C(=O)(O)[O-].[Na+]>C(O)C>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][C:10]=3[CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 57608224HCID 57608224, compound

Product 1

HCID 57608191HCID 57608191, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed solution of 2-(2-(4-fluoro-benzyl)-benzofuran-5-ylmethyl)-isoindole-1,3-dione (81 mg, 0.21 mmol) described in Production Example 76-1-3 in ethanol (5 mL) and tetrahydrofuran (3 mL) was added hydrazine monohydrate (52.6 mg, 1.05 mmol). This mixture was stirred for 3 hours while heating under reflux. After allowing the reaction mixture to cool on standing, saturated aqueous sodium bicarbonate solution was poured thereinto followed by extraction with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl, drying over anhydrous magnesium sulfate and concentrating under a reduced pressure to obtain the title compound (42 mg, 78%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. temperatureto cool
  4. extractionthereinto followed by extraction with ethyl acetate
  5. customThe organic layer was separated
  6. washby washing with sat. NaCl
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. concentrationconcentrating under a reduced pressure

Sources & evidence

ORD record
ord-2dffb1de665147cba9160d3525fd4ec0
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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