1'-(diphenylmethyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)one

HRID 645168Notes

Reaction equation

HRID 645168 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[CH:22][C:23]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:30])C=CC=CC=1.[H][H]>CO.C(O)(=O)C.[Pd]>[F:29][C:26]([F:27])([F:28])[O:25][C:23]1[CH:22]=[CH:21][C:20]2[C:10]3([CH2:17][O:18][C:19]=2[CH:24]=1)[C:11]1[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:9]3=[O:30]

Participants

6

Reactant 2

HCID 592633931'-(diphenylmethyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 119984696-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)oneYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a suspension of 1′-(diphenylmethyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (6.00 g, 12.3 mmol) in methanol (100 mL) and acetic acid (1.00 mL) was added 10% palladium on carbon (0.65 g, 0.62 mmol), and the mixture was hydrogenated at ambient temperature under 130 psi of hydrogen for 5 days. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo to dryness. The residue was subjected to flash chromatography eluting with 30% ethyl acetate in hexane to give the title compound (2.95 g, 75%) as a white solid: mp 180-182° C.; 1H NMR (300 MHz, CDCl3) δ 9.19 (S, 1H), 7.29-6.92 (m., 4H), 6.86-6.64 (m, 3H), 5.03 (d, 1H), 4.75 (d, 1H); 13C NMR(75 MHz, CDCl3) δ 179.9, 161.9, 150.6, 132.3, 129.4, 127.4, 125.6, 124.3, 124.2, 123.8, 120.5, 114.1, 110.7, 104.3, 80.8, 58.2; MS (ES+) m/z 322 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was concentrated in vacuo to dryness
  3. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-61819714089948dea022eb9a4e143d56
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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