Triethyl orthoacetate → 3-((6-(2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)-1H-indol-1-yl)methoxy)benzonitrile

HRID 56241Notes

Reaction equation

[NH2:1]/[C:2](/[CH3:26])=[CH:3]\[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)=[CH:9][CH:8]=1)=[O:5].[C:27](OCC)(OCC)(OCC)[CH3:28]>>[CH3:27][C:28]1[N:6]([C:7]2[CH:15]=[C:14]3[C:10]([CH:11]=[CH:12][N:13]3[CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[C:24]#[N:25])=[CH:9][CH:8]=2)[C:4](=[O:5])[CH:3]=[C:2]([CH3:26])[N:1]=1

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 90030960HCID 90030960, compound

Product 1

HCID 900308963-((6-(2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)-1H-indol-1-yl)methoxy)benzonitrileYield 25%

Conditions

Temperature: 130 °C

Procedure

A mixture of (Z)-3-amino-N-(1-((3-cyanophenoxy)methyl)-1H-indol-6-yl)but-2-enamide (1.04 g, 3.00 mmol) and triethyl orthoacetate (20 mL) was stirred at 130° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (272 mg, 25%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record: ord-fe15daea1c304f1d9d2d0f1f63da566c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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