Sodium Carbonate → HCID 58585765, compound

HRID 1297670Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2Cl)=[O:5])[CH3:2].[CH3:19][CH:20]([CH3:25])[CH2:21]B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COC(OC)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[CH2:19][CH:20]([CH3:25])[CH3:21])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 4-chloro-3-cyano-quinoline-6-carboxylic acid ethyl ester (example 46c, 1.3 g, 5 mmol), (2-methylpropyl)boronic acid (1.0 g, 10 mmol), sodium carbonate (3.18 g, 30 mmol) and POPd (bis[bis(1,1-dimethylethyl)phosphinous acid-κP]dichloropalladium, CAS: 391683-95-7) (75 mg, 0.15 mmol) in dimethyloxyethane (DME) (20 mL) was stirred at 100° C. for 2 days. After cooling to room temperature, the product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-50% ethyl acetate in hexanes in 30 min) afforded 3-cyano-4-isobutyl-quinoline-6-carboxylic acid ethyl ester (1.1 g, 79%) as a clear oil. LC-MS m/e 283 (MH+).

Workup

temperatureAfter cooling to room temperature
extractionthe product was extracted with ethylacetate
washThe combined organic layers were successively washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3800ae7d2c864895a357feae83b7e3cf
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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