Pyridine → N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamide

HRID 347384Notes

Reaction equation

N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]#[C:15][C:16]1[C:17]([O:26][CH3:27])=[CH:18][C:19]([O:24][CH3:25])=[C:20]([CH:23]=1)[CH:21]=[O:22].[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[CH:21]([C:20]1[C:19]([O:24][CH3:25])=[CH:18][C:17]([O:26][CH3:27])=[C:16]([C:15]#[C:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:28](=[O:30])[CH3:29])[CH:23]=1)=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridine (453 μL, 5.61 mmol) was added to a suspension of 5-(2-amino-phenylethynyl)-2,4-dimethoxybenzaldehyde (Ex-35C, 750 mg, 2.67 mmol) in anhydrous methylene chloride (20 mL) and chilled to 0° C. The reaction mixture was treated dropwise with acetyl chloride (9.25 mL, 75.1 mmol). Upon completion the reaction was quenched with IN HCl (10 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to dryness. The crude solid was purified by silica gel chromatography (5% MeOH/CH2Cl2) to yield 671 mg (78%) of N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamide as an off-white solid. 1H-NMR (300 MHz, DMSO-d6) 10.15 (s, 1H), 9.23 (br s, 1H), 7.82 (m, 2H), 7.80 (s, 1H), 7.50 (dd, 1H, J=0.9, 7.8 Hz), 7.35 (dt, 1H, J=1.8, 9.3 Hz), 7.12 (t, 1H, J=7.8 Hz), 6.82 (s, 1H), 4.00 (s, 3.99 (s, 3H), 2.10 (s, 3H).

Workup

customUpon completion the reaction was quenched with IN HCl (10 mL)
customthe layers were separated
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness
customThe crude solid was purified by silica gel chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-0e4caf59ded94fb8a9dc64cd51b6b2ef
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173129B2

Reaction notes

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