But-1-ene-1,3-dione → HCID 90031188, compound

HRID 56239Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-((6-amino-1H-indol-1-yl)methoxy)benzonitrile (2.62 g, 9.95 mmol) in EtOAc (20 mL) was added acetyl ketene (1.0 g, 11.9 mmol) and the mixture was stirred at 80° 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 (2.70 g, 78%).

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-9bf0cfd297aa4358a443e5ed649f84af
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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