Propionic Acid → 9-(1-Acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methyl-pyrimidin-5-yl)-non-4-enoic acid ethyl ester

HRID 860090Notes

Reaction equation

HRID 860090 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14](O)[CH:15]=[CH:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=3)=[CH:8][CH:9]=[C:4]2[CH2:3][CH2:2]1.[C:25](O)(=[O:28])[CH2:26]C.[C:30]([CH3:40])(OCC)([O:34]CC)[O:31][CH2:32][CH3:33]>>[CH2:32]([O:31][C:30](=[O:34])[CH2:40][CH:16]([C:17]1[CH:18]=[N:19][C:20]([CH3:23])=[N:21][CH:22]=1)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[N:6]=[C:5]2[N:1]([C:25](=[O:28])[CH3:26])[CH2:2][CH2:3][C:4]2=[CH:9][CH:8]=1)[CH3:33]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetateHCID 696663717-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-ol

Product 1

HCID 696665499-(1-Acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methyl-pyrimidin-5-yl)-non-4-enoic acid ethyl esterYield 37%

Procedure

A solution of the allylic alcohol 23-9 (0.402 g, 1.24 mmol) in (EtO)3CMe (20 mL) was treated with 1 uL propionic acid. The yellow solution was heated at reflux until complete by 1 cms. The solution was cooled to room temperature, concentrated, and purified by PCTLC (4 mm, 0–10% MeOH/CHCl3) which provided 0.198 g (37% yield) of 23-10.

Workup

  1. temperatureThe yellow solution was heated
  2. temperatureat reflux until complete by 1 cms
  3. concentrationconcentrated
  4. custompurified by PCTLC (4 mm, 0–10% MeOH/CHCl3) which

Sources & evidence

ORD record
ord-8d7aa277ecd6448083aa15c3c2d52d7f
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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