Sesamol → 1-(diphenylmethyl)-3-hydroxy-3-[2-hydroxy-4-(trifluoromethoxy)phenyl]-1,3-dihydro-2H-indol-2-one

HRID 645114Notes

Reaction equation

C1(CCN2C3C(=CC=CC=3)C(=O)C2=O)CC1.[C:17]1([CH:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26](=[O:33])[C:25]2=[O:34])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O1C2C=CC(O)=CC=2OC1.[F:51][C:52]([F:62])([F:61])[O:53][C:54]1[CH:55]=[C:56]([OH:60])[CH:57]=[CH:58][CH:59]=1>>[C:35]1([CH:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([OH:33])([C:57]3[CH:58]=[CH:59][C:54]([O:53][C:52]([F:61])([F:62])[F:51])=[CH:55][C:56]=3[OH:60])[C:25]2=[O:34])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Reactant 4

HCID 68289Sesamol

HCID 19692771-(diphenylmethyl)-1H-indole-2,3-dione

HCID 27332613-(Trifluoromethoxy)phenol

HCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 120043341-(diphenylmethyl)-3-hydroxy-3-[2-hydroxy-4-(trifluoromethoxy)phenyl]-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-(diphenylmethyl)-1H-indole-2,3-dione, and 1,3-benzodioxol-5-ol with 3-(trifluoromethoxy)phenol, the title compound was obtained (75%): MS (ES+) m/z 514.5 (M+23).

Sources & evidence

ORD record: ord-db27bfbf6b374dbcbd78a6113dcd43e8
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700641B2

Reaction notes

Loading…