Water → HCID 59810801, compound

HRID 2240169Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH2:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20](=[O:22])[CH3:21])=[CH:17][CH:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:12]=1)[CH3:10].O.C(OCC)(=O)C>CN(C)C=O>[CH3:3][N:4]([CH3:6])/[CH:5]=[CH:21]/[C:20]([C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH2:9][CH3:10])=[N:12][N:13]2[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:18][CH:17]=1)=[O:22]

Participants

Conditions

Temperature: 140 °C

Procedure

Under an atmosphere of argon, 1,1-Dimethoxy-N,N-dimethylmethanamine (4.4 mL, 0.033 mol) and 1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)ethanone (3.5 g, 0.011 mol) were mixed in N,N-dimethylformamide (110 mL) and the resulting mixture was heated at 140° C. for 16 hours. After cooling to room temperature, water (250 mL) and ethyl acetate (250 mL) were added, the layers were separated, and the product was extracted with ethyl acetate (3×100 mL). The combined organic layers, were washed with water and brine, dried (sodium sulfate), and the volatiles were removed in vacuo to afford 4.1 g (quantitative yield) of (2E)-3-(dimethylamino)-1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)prop-2-en-1-one, which was used without further purification.

Workup

temperatureAfter cooling to room temperature
customthe layers were separated
extractionthe product was extracted with ethyl acetate (3×100 mL)
washThe combined organic layers, were washed with water and brine
dry with materialdried (sodium sulfate)
customthe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-7743b9312fa34b8c8eab1d3e7248a0c1
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723348B2

Reaction notes

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