Benzofuran → HCID 18518550, compound

HRID 1369114Notes

Reaction equation

HRID 1369114 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Li]CCCC.[CH2:15]([N:17]([CH2:32][CH3:33])[CH2:18][CH2:19][N:20]1[C:30]2[C:25](=[C:26]([Br:31])[CH:27]=[CH:28][CH:29]=2)[C:23](=[O:24])[C:21]1=[O:22])[CH3:16].[NH4+].[Cl-]>C1COCC1>[CH2:32]([N:17]([CH2:15][CH3:16])[CH2:18][CH2:19][N:20]1[C:30]2[C:25](=[C:26]([Br:31])[CH:27]=[CH:28][CH:29]=2)[C:23]([OH:24])([C:5]2[O:1][C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[CH:4]=2)[C:21]1=[O:22])[CH3:33]

Participants

6

Reactant 4

HCID 9223BenzofuranHCID 25517Ammonium ChlorideHCID 10958318HCID 10958318, compoundHCID 178418339Butyllithium

Product 1

HCID 18518550HCID 18518550, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To benzo[b]furan (76.4 mg, 2.1 eq) in anhydrous THF (2 mL) at −40° C. (bath temperature) was added n-BuLi (0.423 mL, 1.53 M in hexanes, 2.1 eq). The resulting light yellow coloured solution was stirred for 30 minutes, after which 1-(2-diethylaminoethyl)-4-bromoisatin (100.0 mg, 3.08×10−4 mol) in anhydrous THF (2 mL) was added. Stirring was continued at −40° C. for 9 hours. Saturated aqueous NH4Cl (1.5 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration, the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, eluting 1%-2% MeOH in CHCl3) to give the title compound as a yellow oil (29.0 mg, 21%).

Workup

  1. stirringStirring
  2. waitwas continued at −40° C. for 9 hours
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customPurification
  8. washwas carried out by column chromatography (silica gel, eluting 1%-2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-8d91b6f526544b499b7203a9129bea33
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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