Water → 5-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 347385Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

N-[2-(5-Formyl-2,4-dimethoxy-phenyl ethynyl)phenyl]acetamide (Ex-57E, 535 mg, 1.6 mmol) was added to 150 mL of DMF (nitrogen purged) at room temperature and the resulting solution was heated to 80° C. Palladium(II) chloride (22 mg) was added in one portion. After 6 h the reaction mixture was poured into water (50 mL) and EtOAc (50 mL), and the layers were cut. The organic layer was filtered through Celite, washed with brine, and concentrated to an orange solid. The crude was purified by silica gel chromatography (25% ethyl acetate/hexane) to yield 210 mg (39%) of 5-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde as a white solid. 1H-NMR (300 MHz, DMSO-d6) 10.22 (s, 1H), 8.13 (d, 1H, J=8.1 Hz), 7.71 (s, 1H), 7.55 (d, 1H, J=6.3 Hz), 7.25 (m, 2H, J=6.9 Hz), 6.84 (s, 1H), 6.64 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 2.13 (s, 3H).

Workup

filtrationThe organic layer was filtered through Celite
washwashed with brine
concentrationconcentrated to an orange solid
customThe crude was purified by silica gel chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1694fb05fc7d4adeb6d8af77eb19a6be
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173129B2

Reaction notes

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