Maleic Anhydride → 3,5-bis(6-fluoro-1-benzyl-3-indolyl)-2(3H)-furanone

HRID 616785Notes

Reaction equation

HRID 616785 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:18]([CH2:22][C:23]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:26]=3)=O)[C:19]([OH:21])=[O:20])=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C1(=O)OC(=O)C=C1.FC1C=C2C(C=CN2CC2C=CC=CC=2)=CC=1.C(N1C2C(=CC=CC=2)C(C(CC(C2C3C(=CC=CC=3)N(CC)C=2C)=O)C(O)=O)=C1C)C>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:18]3[CH:22]=[C:23]([C:25]4[C:33]5[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=5)[N:27]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:26]=4)[O:20][C:19]3=[O:21])=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 7923Maleic AnhydrideHCID 198699506-Fluoro-1-benzylindoleHCID 204427382,4-Bis(6-fluoro-1-benzyl-3-indolyl)-4-oxobutanoic acidHCID 204427762,4-Bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid

Product 1

HCID 204427903,5-bis(6-fluoro-1-benzyl-3-indolyl)-2(3H)-furanone

Procedure

Following a procedure similar to that described above in part A of this example except that 2,4-bis(6-fluoro-1-benzyl-3-indolyl)-4-oxobutanoic acid prepared by interaction of maleic anhydride and 6-fluoro-1-benzylindole by a procedure similar to that described in Example 3, part A is used in place of 2,4-bis(1-ethyl-2-methyl-3-indolyl)-4-oxobutanoic acid, there is obtained 3,5-bis(6-fluoro-1-benzyl-3-indolyl)-2(3H)-furanone (Formula II: R=C6H5CH2 ; R1 =H; Y=6-F).

Sources & evidence

ORD record
ord-0740a8197b0c49ac9e0ce89fb7e8dd87
Source dataset
uspto-grants-1978_02
Patent number
US04075224

Reaction notes

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