Sodium hydride → 6-{[5-(trifluoromethyl)furan-2-yl]methyl}-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione

HRID 1407423Notes

Reaction equation

HRID 1407423 reaction equation
[O:1]1[C:6]2=[CH:7][C:8]3[C:9](=[O:15])[C:10](=[O:14])[NH:11][C:12]=3[CH:13]=[C:5]2[O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:19][C:20]1[O:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=1>CN(C)C=O>[F:26][C:25]([F:28])([F:27])[C:22]1[O:21][C:20]([CH2:19][N:11]2[C:12]3[CH:13]=[C:5]4[O:4][CH2:3][CH2:2][O:1][C:6]4=[CH:7][C:8]=3[C:9](=[O:15])[C:10]2=[O:14])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20298022,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dioneHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furan

Product 1

HCID 685985666-{[5-(trifluoromethyl)furan-2-yl]methyl}-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione (Lackey and Sternbach, Synthesis 1993:993-997) (3.08 g, 15.0 mmol) in dry N,N-dimethylformamide (150 mL) was added sodium hydride (0.9 g, 60% in mineral oil, 22.5 mmol) at ambient temperature. The deep purple mixture was stirred for 20 min followed by the addition of 2-(bromomethyl)-5-(trifluoromethyl)furan (3.80 g, 16.5 mmol) in one portion. The dark solution was stirred at ambient temperature for 1 h and concentrated in vacuo to dryness. The residue was mixed with water (150 mL) and stirred. The fine orange precipitation was filtered off and dried to afford 6-{[5-(trifluoromethyl)furan-2-yl]methyl}-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione (4.13 g, 78%): 1H NMR (300 MHz, CDCl3) δ7.18 (s, 1H), 6.76-6.73 (m, 1H), 6.48 (s, 1H), 6.45-6.40 (m, 1H), 4.85 (s, 2H), 4.42-4.32 (m, 2H), 4.28-4.20 (m, 2H).

Workup

  1. stirringThe dark solution was stirred at ambient temperature for 1 h
  2. concentrationconcentrated in vacuo to dryness
  3. additionThe residue was mixed with water (150 mL)
  4. stirringstirred
  5. customThe fine orange precipitation
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-b1dc0edb475348e7800e066816f9cf4d
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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