Sesamol → 4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one

HRID 1259631Notes

Reaction equation

HRID 1259631 reaction equation
C1(CCN2C3C(=CC=CC=3)C(=O)C2=O)CC1.[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20](=[O:35])[C:21](=[O:34])[N:22]2[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.O1C2C=CC(O)=CC=2OC1.[O:46]1[C:50]2[CH:51]=[C:52]([OH:55])[CH:53]=[CH:54][C:49]=2[CH2:48][CH2:47]1>>[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([OH:35])([C:53]1[C:52]([OH:55])=[CH:51][C:50]3[O:46][CH2:47][CH2:48][C:49]=3[CH:54]=1)[C:21](=[O:34])[N:22]2[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

5

Reactant 4

HCID 68289SesamolHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 284924914-bromo-1-(Pyridin-2-ylmethyl)-1H-indole-2,3-dioneHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 588725084-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1-(pyridin-2-ylmethyl)-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 4-bromo-1-(pyridin-2-ylmethyl)-1H-indole-2,3-dione, and 1,3-benzodioxol-5-ol with 2,3-dihydrobenzofuran-6-ol, the title compound was obtained (91%) as a colorless solid: mp >225° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.29 (s, 1H), 8.54 (d, 1H), 7.70 (dt, 1H), 7.61 (br, 1H), 7.32-7.26 (m, 2H), 7.07 (d, 1H), 7.00 (d, 1H), 6.72 (d, 1H), 6.60 (br, 1H), 6.02 (s, 1H), 4.91 (ABq, 2H), 4.47 (t, 2H), 3.06 (d, 2H); 13C NMR (75 MHz, DMSO-d6) δ 176.9, 160.4, 156.3, 153.8, 149.6, 146.1, 137.5, 130.9, 130.8, 126.5, 125.8, 123.1, 121.5, 118.8, 117.3, 116.4, 108.3, 96.7, 76.6, 71.9, 45.7, 29.1; MS (ES+) m/z 455.4 (M+1), 437.4 (M−17).

Sources & evidence

ORD record
ord-044106343a1b462e8edd783f6b2574dc
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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