Hydrochloric Acid → HCID 67314726, compound

HRID 1011390Notes

Reaction equation

HRID 1011390 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:21][C:22]1[C:23]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:29][C:28](=O)[C:24]=2[CH:25]=[N:26][CH:27]=1.Cl>C1COCC1>[Br:21][C:22]1[C:23]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:29][C:28](=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[C:24]=2[CH:25]=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 2733832Lithium HexamethyldisilazideHCID 67315181HCID 67315181, compound

Product 1

HCID 67314726HCID 67314726, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dihydro-indol-2-one (225 mg, 1.55 mmol) in THF (6 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (3.5 mL of a 1 M solution in THF, 3.5 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 7-bromo-1-phenyl-1H-furo[3,4-c]pyridin-3-one (305 mg, 1.0 mmol, AcOH salt) is added as a solid to the reaction mixture. The resulting solution is stirred for 3.5 h. The reaction mixture is poured into aqueous 10% HCl solution (50 mL) and stirred at room temperature for 48 h. The precipitate which formed is collected by filtration and dried. The solid obtained is purified by chromatography (silica gel, 30% EtOAc/hexane). The product containing fractions are concentrated to give the title compound as a yellow solid (120 mg, 27%).

Workup

  1. stirringThe resulting solution is stirred for 3.5 h
  2. stirringstirred at room temperature for 48 h
  3. customThe precipitate which formed
  4. filtrationis collected by filtration
  5. customdried
  6. customThe solid obtained
  7. customis purified by chromatography (silica gel, 30% EtOAc/hexane)
  8. additionThe product containing fractions
  9. concentrationare concentrated

Sources & evidence

ORD record
ord-e56429a8bd104abda12adf3dbae5b5d7
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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