4'-(3-furyl)-1'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one → HCID 59352720, compound

HRID 2385541Notes

Reaction equation

HRID 2385541 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[C:8]2([C:20]4=[CH:21][C:22]5[O:26][CH2:25][O:24][C:23]=5[CH:27]=[C:19]4[O:18][CH2:17]2)[C:9](=[O:16])[N:10]3[CH3:15])=[CH:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:15][N:10]1[C:11]2[C:7](=[C:6]([CH:3]3[CH2:4][CH2:5][O:1][CH2:2]3)[CH:14]=[CH:13][CH:12]=2)[C:8]2([C:20]3=[CH:21][C:22]4[O:26][CH2:25][O:24][C:23]=4[CH:27]=[C:19]3[O:18][CH2:17]2)[C:9]1=[O:16]

Participants

5

Reactant 2

HCID 592634164'-(3-furyl)-1'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 59352720HCID 59352720, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-furan-3-yl-1′-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.60 g, 1.66 mmol) in ethyl acetate (30 mL) was added palladium on carbon (10% w/w, 0.40 g). The reaction mixture was shaken under a pressure of hydrogen gas (60 psi) in a Parr hydrogenation apparatus at ambient temperature for 16 h and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo and the residue recrystallized from dichloromethane/diethyl ether to afford methyl-4′-(tetrahydrofuran-3-yl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.44 g, 73%) as a colorless solid: mp 182-184° C. (dichloromethane/ether); 1H NMR (300 MHz, CDCl3) δ 7.31-7.35 (m, 1H), 7.08-7.01 (m, 1H), 6.77 (d, J=7.7 Hz, 1H), 6.52-6.48 (m, 1H), 6.15 (d, J=13.3 Hz, 1H), 5.90-5.84 (m, 2H), 4.96 (dd, J=9.26, 1.0 Hz, 1H), 4.78-4.67 (m, 1H), 4.11-3.59 (m, 3H), 3.39-3.18 (m, 2H), 2.40-1.94 (m, 1H), 1.63-1.36 (m, 1H); MS (ES+) m/z 365.9 (M+1).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue recrystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-02c008e3015d4f7cbce513327cf1cc44
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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