Trifluoroacetic acid → 3-(5-hydroxy-3-methyl-1,2-benzisoxazol-6-yl)-1-(4-methoxybenzyl)-1,3-dihydro-2H-indol-2-one

HRID 1965348Notes

Reaction equation

HRID 1965348 reaction equation
O[C:2]1([C:21]2[C:30]([OH:31])=[CH:29][C:24]3[C:25]([CH3:28])=[N:26][O:27][C:23]=3[CH:22]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:3]1=[O:20].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[OH:31][C:30]1[C:21]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:3]2=[O:20])=[CH:22][C:23]2[O:27][N:26]=[C:25]([CH3:28])[C:24]=2[CH:29]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 686020023-hydroxy-3-(5-hydroxy-3-methyl-1,2-benzisoxazol-6-yl)-1-(4-methoxybenzyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 673571923-(5-hydroxy-3-methyl-1,2-benzisoxazol-6-yl)-1-(4-methoxybenzyl)-1,3-dihydro-2H-indol-2-oneYield 92.4%

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 3-hydroxy-3-(5-hydroxy-3-methyl-1,2-benzisoxazol-6-yl)-1-(4-methoxybenzyl)-1,3-dihydro-2H-indol-2-one (0.84 g; 2.0 mmol) in triethylsilane (3.0 mL, 18.7 mmol) was added trifluoroacetic acid (15.0 mL). The reaction mixture was stirred at 50° C. for 26 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was recrystallized from ethyl acetate/hexanes to afford 3-(5-hydroxy-3-methyl-1,2-benzisoxazol-6-yl)-1-(4-methoxybenzyl)-1,3-dihydro-2H-indol-2-one (0.74 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.34-6.80 (m, 10H), 5.29 (s, 1H), 4.87 (ABq, 2H), 3.74 (s, 3H), 2.45 (s, 3H); MS (ES+) m/z 400.9 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-794f2dd828aa4325847ce01799d6769c
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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