Sodium Iodide → 1'-[(6-oxo-1,6-dihydropyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 425693Notes

Reaction equation

HRID 425693 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3([C:22]4=[CH:23][C:24]5[O:28][CH2:27][O:26][C:25]=5[CH:29]=[C:21]4[O:20][CH2:19]3)[C:11]2=[O:30])=[CH:5][CH:4]=1.[I-].[Na+].Cl[Si](C)(C)C>O.C(#N)C>[O:2]=[C:3]1[NH:8][CH:7]=[C:6]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3([C:22]4=[CH:23][C:24]5[O:28][CH2:27][O:26][C:25]=5[CH:29]=[C:21]4[O:20][CH2:19]3)[C:11]2=[O:30])[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 592634711'-[(6-methoxypyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 592633751'-[(6-oxo-1,6-dihydropyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1′-[(6-methoxypyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.23 g, 0.57 mmol), sodium iodide (0.28 g, 1.87 mmol), water (2 drops) in anhydrous acetonitrile (5.00 mL) was added chlorotrimethylsilane (0.19 g, 1.78 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h and quenched with sodium bisulfite (0.20 g). The reaction mixture was diluted with ethyl acetate (100 mL) and washed with brine (2×25.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether (2×10.0 mL) to give the title compound (0.16 g, 72%) as la ight yellow solid: mp 247-250° C.; 1H NMR (300 MHz, DMSO-d6,) δ 11.50 (br, 1H), 7.50 (bd, 1H), 7.36-7.24 (m, 2H), 7.17-7.12 (m, 2H), 7.01 (dt, 1H), 6.67 (s, 1H), 6.28 (d, 1H), 6.09 (s, 1H), 5.91-5.88 (m, 2H), 4.78 (d, 1H), 4.67-4.62 (m, 3H); MS (ES+) m/z 389.15 (M+1).

Workup

  1. customquenched with sodium bisulfite (0.20 g)
  2. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  3. washwashed with brine (2×25.0 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe residue was triturated with ether (2×10.0 mL)

Sources & evidence

ORD record
ord-647e93b1148b4c22bd8b3f29bbae164b
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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