Sodium Bicarbonate → HCID 86615782, compound

HRID 1926131Notes

Reaction equation

I[C:2]1[C:7]([N:8]([CH3:15])[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[C:6]([I:16])[N:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:32]=[CH:31][C:21]([O:22][C:23]2[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=2)[C:26]#[N:27])=[C:20]([Cl:33])[CH:19]=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:33][C:20]1[CH:19]=[C:18]([NH:17][C:2]2[C:7]([N:8]([CH3:15])[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[C:6]([I:16])[N:5]=[CH:4][N:3]=2)[CH:32]=[CH:31][C:21]=1[O:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:25]([C:26]#[N:27])[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(4,6-Diiodopyrimidin-5-yl)-2,2,2-trifluoro-N-methylacetamide (3 g) and 3-(4-amino-2-chlorophenoxy)benzonitrile (1.69 g) were dissolved in 1-methyl-2-pyrrolidone (11.4 mL), and the mixture was stirred with heating at 100° C. for 16 hrs. To the reaction mixture was added aqueous sodium hydrogen carbonate (80 mL) and the mixture was extracted with ethyl acetate (100 mL×2). The organic layer was washed with saturated brine (80 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→hexane:ethyl acetate=50:50) and crystallized from diisopropyl ether to give the title compound (1.67 g) as colorless crystals.

Workup

extractionthe mixture was extracted with ethyl acetate (100 mL×2)
washThe organic layer was washed with saturated brine (80 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→hexane:ethyl acetate=50:50)
customcrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-7f19390d86df4b78aa9ba261670855ab
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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