Indole → HCID 57120626, compound

HRID 439855Notes

Reaction equation

HRID 439855 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[C:5]2[C:18](=[CH:19][C:20]=1[CH3:21])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][C:15]=3[C:7]=1[CH2:6]2.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+].N1C2C(=CC=CC=2)C=C1>FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[C:5]2[C:18](=[CH:19][C:20]=1[CH3:21])[C@H:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][C:15]=3[C@H:7]1[CH2:6]2

Participants

7

Reactant 4

HCID 798IndoleHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22408472HCID 22408472, compound

Product 1

HCID 57120626HCID 57120626, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5,10-Dihydro-2,8-dimethoxy-1,3-dimethylindeno[1,2-b]indole (1.04 g, 3.55 mmol) was dissolved in trifluoroacetic acid (5 cm3) and triethylsilane (0.6 cm3) added with vigorous stirring. Stirring was continued for 4 hours, and the reaction worked up incomplete due to the appearance by t.l.c. of impurities. The solution was poured into water, stirred, and brought to pH 7.0 with solid sodium bicarbonate. The organic material was extracted into DCM, which was washed with sodium bicarbonate solution, and filtered through phase separating filter paper. The product and starting material were separated by column chromatography eluting with 20% EtOAc/60°-80° petrol to yield starting indole (0.06 g, 6%) and a colourless solid. Yield: 0.57 g, 58% .M.p. 149-50° C. (from EtOAc/petrol). 1H NMR (CDCl3) δ: 6.99 (1H, s), 6.79 (1H, m), 6.57 (2H, m), 5.18 (1H, d, J=8.5 Hz), 4.18 (1H, dd(br)), 3.74 (3H, s), 3.65 (3H, s), 3.35 (1H, dd, 3J=8.4 Hz), 3.06 (1H, d(d)), 2.25 (3H, s), 2.15 (3H, s).

Workup

  1. stirringstirred
  2. extractionThe organic material was extracted into DCM, which
  3. washwas washed with sodium bicarbonate solution
  4. filtrationfiltered through phase
  5. customseparating
  6. filtrationfilter paper
  7. customwere separated by column chromatography
  8. washeluting with 20% EtOAc/60°-80° petrol
  9. customto yield

Sources & evidence

ORD record
ord-c3ccc01d61a64161910a95131da6c59f
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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