Ethyl Acetate → HCID 69673892, compound

HRID 2276330Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]3[C:14]([CH:13]=[CH:12][CH:11]=[CH:10]3)=[C:6]2[N:5]=[C:4]([CH3:15])[C:3]=1[CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18].[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>O.COCCOC>[CH3:15][C:4]1[C:3]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[C:2]([C:28]2[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=2)[N:7]2[N:8]=[C:9]3[C:14]([CH:13]=[CH:12][CH:11]=[CH:10]3)=[C:6]2[N:5]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a sonicated solution of methyl 2-(4-chloro-2-methylpyrimido[1,2-b]indazol-3-yl)pentanoate (0.252 g; 0.74 mmol) and 4-methylphenylboronic acid (0.201 mg; 1.48 mmol) in a mixture of water/DME (⅓, 3 mL) were added palladiumtetrakistriphenylphosphine (0.128 mg; 0.11 mmol) and diisopropylethylamine (0.368 mL; 2.22 mmol). The solution was stirred for 20 min at 140° C. under microwave irradiation. Ethyl acetate was added to the reaction mixture and the solution was washed with a 1N hydrochloric acid solution, a 1N sodium hydrogenocarbonate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1-40%) in dichloromethane furnished 0.264 g (90%) of methyl 2-(2-methyl-4-p-tolylpyrimido[1,2-b]indazol-3-yl)pentanoate as an oil. ESI/APCI(+): 388 (M+H).

Workup

washthe solution was washed with a 1N hydrochloric acid solution
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (1-40%) in dichloromethane

Sources & evidence

ORD record: ord-f4ccf37c05974d969c44d9cb2ec6ab46
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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