Ammonium fluoride → HCID 69516446, compound

HRID 855015Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC.[F-].[NH4+]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]([C:14]([F:17])([F:16])[F:15])[O:8]2)=[CH:3][C:2]=1[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of 0.3 g (0.7 mmol) ethyl 6-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate and 16 mg (0.0139 mmol) tetrakis(triphenyl-phosphine)-palladium(0) in 4.2 mL of anhydrous toluene under nitrogen atmosphere was added 228 uL (0.785 mmol ) tributyl(vinyl)tin. The resulting solution was heated to 115° C. for three h. To the cooled reaction mixture was added 20 ml of 20% ammonium fluoride. After stirring for 15 min, the product was extracted three times with ethyl acetate. The combined organic extracts were washed twice with 20% ammonium fluoride, washed with brine and dried over anhydrous magnesium sulfate. The crude product was purified by silica chromatography with EtOAc/hexane (1:9) and used directly in the next step.

Workup

customTo the cooled reaction mixture
extractionthe product was extracted three times with ethyl acetate
washThe combined organic extracts were washed twice with 20% ammonium fluoride
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe crude product was purified by silica chromatography with EtOAc/hexane (1:9)

Sources & evidence

ORD record: ord-e766a2d53aa841b1826837ffa10392a3
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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