(diphenylmethyl)-5'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one → 5'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 645161Notes

Reaction equation

HRID 645161 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[C:10]3([C:21]4=[CH:22][C:23]5[O:27][CH2:26][O:25][C:24]=5[CH:28]=[C:20]4[O:19][CH2:18]3)[C:9]2=[O:29])C=CC=CC=1>[OH-].[Pd+2].[OH-].C(O)(=O)C>[CH3:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][C:9](=[O:29])[C:10]12[C:21]2=[CH:22][C:23]3[O:27][CH2:26][O:25][C:24]=3[CH:28]=[C:20]2[O:19][CH2:18]1

Participants

4

Reactant 1

HCID 59263474(diphenylmethyl)-5'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 592634415'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneYield 43.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A stainless steel hydrogenating vessel was successively charged with 1′-(diphenylmethyl)-5′-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.90 g, 1.95 mmol), glacial acetic acid (50.0 mL) and palladium hydroxide (0.10 g, 1.35 mmol, 20 wt % on carbon). The vessel was flushed with nitrogen, sealed then heated to 60° C. and placed under 120 Psi of H2. After 4 days of stirring, the reaction mixture was diluted with ethyl acetate and passed through a bed of celite. The filtrate was washed with water (6×100 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with ethyl acetate/hexane (40-50%) to afford the title compound (0.25 g, 43%): mp 269-271° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.45 (s, 1H), 7.00 (d, 1H), 6.87 (s, 1H), 6.76 (d, 1H), 6.63 (s, 1H), 6.21 (s, 1H), 5.87 (d, 2H), 4.64 (ABq, 2H), 2.17 (s, 3H); MS (ES+) m/z 296.28 (M+1).

Workup

  1. customThe vessel was flushed with nitrogen
  2. customsealed
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washThe filtrate was washed with water (6×100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness
  8. washeluting with ethyl acetate/hexane (40-50%)

Sources & evidence

ORD record
ord-7888c0ddba1f4f5f960440bc3f32c8eb
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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