Ethyl Acetate → 2-Fluoro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 473649Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][C:8](OS(C(F)(F)F)(=O)=O)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F:19][C:20]1[C:25](B(O)O)=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:19][C:20]1[C:25]([C:8]2[CH2:9][CH2:10][C:5]3([O:1][CH2:2][CH2:3][O:4]3)[CH2:6][CH:7]=2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of 1,4-dioxaspiro[4.5]dec-7-en-8-yltrifluoromethanesulfonate (10.2 g, 35.4 mmol) and 2-fluoropyridin-3-ylboronic acid (5.00 g, 35.5 mmol) in 1,2-dimethoxyethane (200 mL) and aqueous sodium carbonate (53.2 mL, 106 mmol, 2N) under argon atmosphere was added palladium tetrakis(triphenylphosphine) (1.23 g, 1.06 mmol). The mixture was heated and stirred at 85° C. for 1 h., then cooled to room temperature. Ethyl acetate was added and the mixture was washed with water (2×), saturated sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 2-fluoro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine. MS (ESI, pos. ion) m/z: 236.1.

Workup

temperatureThe mixture was heated
temperaturecooled to room temperature
washthe mixture was washed with water (2×), saturated sodium chloride (1×)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record: ord-dcbeb14c1eb441a8992d4bd8154fb9a4
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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