3-Bromomethylpropionate → 4-methoxybenzyl (E)-4-[3-[4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoyl]1-indolyl]butyrate

HRID 260853Notes

Reaction equation

HRID 260853 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:16][CH2:17]/[CH:18]=[CH:19]/[C:20]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(C1C2C(=CC=CC=2)NC=1)(=O)CCCCCC.Br[CH2:49][CH2:50][CH2:51][C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=1)=[O:53].BrCCCC([O-])=O>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([O:16][CH2:17]/[CH:18]=[CH:19]/[C:20]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH2:49][CH2:50][CH2:51][C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=3)=[O:53])[CH:23]=2)=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 69936583-BromomethylpropionateHCID 224004583-HeptanoylindoleHCID 224004624-Methoxybenzyl 4-bromobutyrateHCID 22400532(E)-3-[4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoyl]indole

Product 1

HCID 867495864-methoxybenzyl (E)-4-[3-[4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoyl]1-indolyl]butyrate

Procedure

The procedure of Ex. 1 was repeated except that (E)-3-[4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoyl]indole obtained in Step 4 of Pre. Ex. 19 was used in place of 3-heptanoylindole, and 4-methoxybenzyl 4-bromobutyrate obtained in Step 5 of Pre. Ex. 19 was used in place of 4-bromobutyrate to give 4-methoxybenzyl (E)-4-[3-[4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoyl]1-indolyl]butyrate as an oil.

Sources & evidence

ORD record
ord-8f199d4c2ddc47aeae693f74e8f60d27
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

Loading…