Potassium Carbonate → (3,5-Bis(trifluoromethyl)phenyl}-7-chlorofuro[2,3-c]pyridine

HRID 389487Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9](I)[O:8][C:7]=12.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.C([O-])([O-])=O.[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1.O>[F:12][C:13]([F:27])([F:28])[C:14]1[CH:15]=[C:16]([C:9]2[O:8][C:7]3=[C:2]([Cl:1])[N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=2)[CH:17]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a three-neck flask was placed a mixture of 7-chloro-2-iodofuro[2,3-c]pyridine (1.00 g, 3.58 mmol), 3,5-bis(trifluoromethyl)phenyl boronic acid (0.92 g, 3.6 mmol), 1,4-dioxane/water (50 mL/10 mL) and K2CO3 (0.74 g, 5.38 mmol). After the suspension was degassed with nitrogen for 15 min, (PPh3)2PdCl2 (0.12 g, 0.17 mmol) was added and the mixture was degassed with nitrogen for 5 min. The resultant mixture was stirred at 50° C. for 48 h under nitrogen. The mixture was then cooled to RT and the solvent was evaporated to give a black residue, which was purified by flash chromatography (2% MeOH:DCM) to afford 965 mg (74%) of the title compound as a white crystalline. 1H NMR (300 MHz, CDCl3): δ 7.06 (s, 1H), 7.50 (m, 4H), 7.94 (dd, J=1.5 Hz, 2.4 Hz, 1H), 8.19 (d, J=5.1 Hz, 1H).

Workup

customIn a three-neck flask was placed
customAfter the suspension was degassed with nitrogen for 15 min
customthe mixture was degassed with nitrogen for 5 min
temperatureThe mixture was then cooled to RT
customthe solvent was evaporated
customto give a black residue, which
customwas purified by flash chromatography (2% MeOH:DCM)

Sources & evidence

ORD record: ord-c49d961a8ee54eefae68310c94485e9a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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