Cesium carbonate → ethyl 7-pyrrolidin-1-yl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854969Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>C1(C)C=CC=CC=1.CCCCCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:40]1([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]3)=[CH:4][CH:3]=2)[CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

Conditions

Temperature: 75 °C

Procedure

Ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.40 g, 1.0 mmol), was dissolved in 3 mL toluene, followed by the addition of Pd(OAc)2 (23 mg), P(t-Bu)3, 10 wt % in hexane (0.21 g), Cs2CO3 (0.56 g, 1.7 mmol) and pyrrolidine (0.10 g, 1.4 mmol), in a sealed tube flushed with argon, and stirred vigorously while heating to 75° C. for 21 hours. The reaction was cooled, filtered, and stripped, leaving a dark red-orange oil, which was purified by flash chromatography, which gave ethyl 7-pyrrolidin-1-yl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.27 g, 0.79 mmol) as a yellow solid. The product structure was consistent with 1H, 19F and 13C NMR analyses.

Workup

temperatureThe reaction was cooled
filtrationfiltered
customleaving a dark red-orange oil, which
customwas purified by flash chromatography, which

Sources & evidence

ORD record: ord-78b96d05c43f49648bba05e0f282042e
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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