Sesamol → 3-(4,5-difluoro-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 425473Notes

Reaction equation

HRID 425473 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[C:7]2=[O:16])[CH2:3][CH2:2]1.C(N1C2C(=CC=CC=2)C(=O)C1=O)CCCC.O1C2C=CC(O)=CC=2OC1.[F:43][C:44]1[CH:45]=[C:46]([OH:51])[CH:47]=[CH:48][C:49]=1[F:50]>>[F:43][C:44]1[C:49]([F:50])=[CH:48][C:47]([C:8]2([OH:15])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:6]([CH2:5][CH2:4][CH2:1][CH2:3][CH3:2])[C:7]2=[O:16])=[C:46]([OH:51])[CH:45]=1

Participants

5

Reactant 4

HCID 68289SesamolHCID 759273,4-DifluorophenolHCID 15810921-Pentyl-1H-indole-2,3-dioneHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 120043033-(4,5-difluoro-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with 1-pentyl-1H-indole-2,3-dione, and 1,3-benzodioxol-5-ol with 3,4-difluorophenol, the title compound was obtained (31%): 1H NMR (300 MHz, CDCl3) δ 9.69-9.65 (br, 1H), 7.51-7.41 (m, 2H), 7.26-7.21 (m, 1H), 6.99-6.57 (m, 3H), 4.18-4.14 (br, 1H), 3.78-3.58 (m, 2H), 1.76-1.62 (m, 2H), 1.40-1.28 (m, 4H), 0.87 (t, 3H); MS (ES+) m/z 330 (M−17), 370 (M+23).

Sources & evidence

ORD record
ord-ffb70232c70f472492eec2949e89bba8
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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