3-Bromomethylpropionate → (E)-4-methoxybenzyl 4-[3-(2-nonenoyl)-1-indolyl]butyrate

HRID 260855Notes

Reaction equation

[C:1]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(C1C2C(=CC=CC=2)NC=1)(=O)CCCCCC.Br[CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)=[O:42].BrCCCC([O-])=O>>[C:1]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[O:42])[CH:12]=1)(=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 4

HCID 69936583-Bromomethylpropionate

HCID 224004583-Heptanoylindole

HCID 224004624-Methoxybenzyl 4-bromobutyrate

HCID 22400476(E)-3-(2-nonenoyl) indole

Product 1

HCID 22400455(E)-4-methoxybenzyl 4-[3-(2-nonenoyl)-1-indolyl]butyrate

Procedure

The procedure of Ex. 1 was repeated except that (E)-3-(2-nonenoyl) indole obtained in Pre. Ex. 22 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 (E)-4-methoxybenzyl 4-[3-(2-nonenoyl)-1-indolyl]butyrate as an oil.

Workup

customobtained in Pre

Sources & evidence

ORD record: ord-1ba234787f494cc49154052db0dc8dcb
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05530019

Reaction notes

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