Sodium Carbonate → HCID 66748390, compound

HRID 1464973Notes

Reaction equation

I[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])[N:19]=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:3]=1.[CH3:27][O:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:23]([O:22][C:20]1[N:19]=[CH:18][N:17]=[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:4]3[CH:3]=[C:2]([C:32]4[CH:33]=[N:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=4)[N:6]([CH3:7])[N:5]=3)=[O:9])[CH2:11][CH2:12]2)[CH:21]=1)[CH:24]([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (5-iodo-1-methyl-1H-pyrazol-3-yl) (4-(6-isobutoxypyrimidin-4-yl)piperazin-1-yl)methanone (20 mg, 0.043 mmol), (6-methoxypyridin-3-yl)boronic acid (8.5 mg, 0.055 mmol), palladium acetate (1.9 mg), triphenylphosphine (4.5 mg), and sodium carbonate (18 mg, 0.17 mmol) in dioxane-THF-water (1.6 mL, 1:0.3:0.3) was stirred at 150° C. for 10 min under microwave irradiation. After cooling to rt, the mixture was poured onto water, and the aqueous layer was extracted with EtOAc (three times). The combined organic layer was concentrated in vacuo. The residue was purified by preparative LC-MS to give 6.5 mg (34% yields) of the title compound.

Workup

temperatureAfter cooling to rt
additionthe mixture was poured onto water
extractionthe aqueous layer was extracted with EtOAc (three times)
concentrationThe combined organic layer was concentrated in vacuo
customThe residue was purified by preparative LC-MS
customto give

Sources & evidence

ORD record: ord-d93e91e66c7f4fe6b945450df16ad9b8
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999974B2

Reaction notes

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