Dimethylformamide → 1'-(diphenylmethyl)-5'-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

HRID 2385184Notes

Reaction equation

HRID 2385184 reaction equation
[CH2:1](N(CC)CC)C.CN(C)C=O.C[Sn](C)(C)C.[C:18]1([CH:24]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:25]2[C:33]3[C:28](=[CH:29][C:30](Br)=[CH:31][CH:32]=3)[C:27]3([C:46]4[C:37](=[CH:38][C:39]5[O:44][CH2:43][CH2:42][O:41][C:40]=5[CH:45]=4)[O:36][CH2:35]3)[C:26]2=[O:47])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[C:18]1([CH:24]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:25]2[C:33]3[C:28](=[CH:29][C:30]([CH3:1])=[CH:31][CH:32]=3)[C:27]3([C:46]4[C:37](=[CH:38][C:39]5[O:44][CH2:43][CH2:42][O:41][C:40]=5[CH:45]=4)[O:36][CH2:35]3)[C:26]2=[O:47])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11661TetramethyltinHCID 593524491'-(diphenylmethyl)-5'-bromo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 593527731'-(diphenylmethyl)-5'-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-oneYield 86%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a 10 mL reaction vessel was added tri-o-tolylphosphine (0.022 g, 0.075 mmol), palladium acetate trimer (0.013 g, 0.020 mmol), triethylamine (0.13 g, 1.30 mmol), N,N-dimethylformamide (1.5 mL), tetramethyltin (0.20 g, 1.1 mmol) and 1′-(diphenylmethyl)-5′-bromo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.50 g, 0.93 mmol). The reaction vessel was sealed, heated at 110° C. for 16 h, allowed to cool to ambient temperature and poured into water (50 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were washed with brine (2×50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with 15% ethyl acetate in hexanes followed by recrystallization from diethyl ether to afford 1′-(diphenylmethyl)-5′-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.38 g, 86%) as a colorless solid: MS (ES+) m/z 476.0 (M+1).

Workup

  1. customTo a 10 mL reaction vessel
  2. customThe reaction vessel was sealed
  3. temperatureto cool to ambient temperature
  4. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic extracts were washed with brine (2×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluted with 15% ethyl acetate in hexanes
  11. customfollowed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-bf2f1c72b9fc43b0bc2fadb39cda5731
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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