Sodium Bicarbonate → HCID 86615782, compound

HRID 1787045Notes

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 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 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-7a8c24dac5c44e08bce93d42fbb68e1b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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