3-(hydroxymethyl)-3-[2-hydroxy-5-(trifluoromethyl)phenyl]-1-pentyl-1,3-dihydro-2H-indol-2-one → 1'-pentyl-5-(trifluoromethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 425606Notes

Reaction equation

HRID 425606 reaction equation
[OH:1][CH2:2][C:3]1([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4]1=[O:17].C1(CCN2C3C(=CC=CC=3)C(C3C(O)=CC4OCOC=4C=3)(CO)C2=O)CC1>>[CH2:12]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2([C:18]3[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:19]=3[O:1][CH2:2]2)[C:4]1=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 588724753-(hydroxymethyl)-3-[2-hydroxy-5-(trifluoromethyl)phenyl]-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 666425671-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 592634221'-pentyl-5-(trifluoromethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 27%

Procedure

Following the procedure as described in Example 1, and making non-critical variations using 3-(hydroxymethyl)-3-[2-hydroxy-5-(trifluoromethyl)phenyl]-1-pentyl-1,3-dihydro-2H-indol-2-one to replace 1-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained in 27% yield: 1H NMR (300 MHz, CDCl3) δ 7.48 (dd, 1H), 7.35 (td, 1H), 7.16-6.90 (m, 5H), 5.02 (d, 1H), 4.76 (d, 1H), 3.91-3.65 (m, 2H), 1.82-1.67 (m, 2H), 1.47-1.29 (m, 4H), 0.91 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.5, 163.3, 142.6, 131.8, 129.8, 129.3, 127.7, 124.1, 124.0, 123.9, 123.6, 121.0, 110.6, 108.9, 80.5, 57.6, 40.5, 29.0, 27.1, 22.3, 13.9; MS (ES+) m/z 376 (M+1).

Sources & evidence

ORD record
ord-b7bbfe90fe6a4c879ee30ab0c15746e5
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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