Sodium hydride → 5'-methyl-1'-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 545836Notes

Reaction equation

HRID 545836 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]12[C:17]2=[CH:18][C:19]3[O:23][CH2:22][O:21][C:20]=3[CH:24]=[C:16]2[O:15][CH2:14]1.Br[CH2:26][C:27]1[O:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=1>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:26][C:27]1[O:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=1)[C:8](=[O:13])[C:7]12[C:17]2=[CH:18][C:19]3[O:23][CH2:22][O:21][C:20]=3[CH:24]=[C:16]2[O:15][CH2:14]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 592634415'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 592633615'-methyl-1'-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.03 g, 0.63 mmol, 60% dispersion in mineral oil) in N,N-dimethylformamide (5.00 mL) was slowly added a solution of 5′-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.10 g, 0.33 mmol) in N,N-dimethylformamide (5.00 mL) at 0° C. After stirring for 15 minutes at 0° C., a solution of 2-(bromomethyl)-5-(trifluoromethyl)furan (0.11 g, 0.49 mmol) in N,N-dimethylformamide (40.0 mL) was added. The resulting mixture was stirred at ambient temperature for 4 h and quenched with water (20.0 mL). The mixture was extracted with ethyl acetate (3×25.0 mL). The combined organic layers was washed with water (50.0 mL) and brine (2×25.0 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was subjected to column chromatography eluting with ethyl acetate/hexane (15-50%) to afford the title compound (0.11 g, 77% yield): mp 96-98° C.; 1H NMR (300 MHz, CDCl3) δ 7.09 (d, 1H), 7.00 (s, 1H), 6.87 (d, 1H), 6.74 (d, 1H), 6.52 (s, 1H), 6.38 (d, 1H), 6.11 (s, 1H), 5.88 (d, 2H), 4.96 (ABq, 2H), 4.80 (ABq, 2H), 2.29 (s, 3H); MS (ES+) m/z 444.2 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 4 h
  2. customquenched with water (20.0 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×25.0 mL)
  4. washThe combined organic layers was washed with water (50.0 mL) and brine (2×25.0 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. washeluting with ethyl acetate/hexane (15-50%)

Sources & evidence

ORD record
ord-54f117cf56544915a91eaedd26e4dc44
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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