Sodium Carbonate → HCID 11300927, compound

HRID 1294680Notes

Reaction equation

[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][N:14]=1.[C:20]([O-:23])([O-])=O.[Na+].[Na+]>CN(C=O)C>[O:23]([C:16]1[CH:17]=[CH:18][C:13]([O:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[N:14][CH:15]=1)[C:20]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Hydroxy quinuclidine (Aldrich, 3.2 g, 25 mmol)) in DMF (anhydrous, 30 mL) was treated with NaH (Aldrich, 99%, 1.2 g, 50 mmol) at ambient temperature for 1 hour. 2-Chloro-5-bromopyridine (7.1 g, 30 mmol) was added and the mixture was stirred at 100° C. for 6 hours. The mixture was allowed to cool to room temperature, treated with Na2CO3 (2M, 10 mL) at 10° C., and extracted with ethyl acetate (2×50 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:2, Rf. 0.20) as oil (5.3 g, yield, 75%). 1H NMR (MeOH-d4, 300 MHz) δ 1.46–1.58 (m, 1H), 1.60–1.88 (m, 2H), 1.96–2.10 (m, 1H), 2.24–2.30 (m, 1H), 2.72–2.98 (m, 5H), 3.42–3.46 (m, 1H), 5.00–5.08 (m, 1H), 6.75 (d, J=8.8 Hz, 1H), 7.77 (dd, J=8.9, 2.4 Hz, 1H), 8.16 (d, J=2.7, 1H) ppm. MS (DCl/NH3) m/z 283 (M+H)+, 285 (M+H)+

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate (2×50 mL)
concentrationconcentrated under reduced pressure
customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:2, Rf. 0.20) as oil (5.3 g, yield, 75%)

Sources & evidence

ORD record: ord-7efed8b645ad455a84bd3cb1f4126ec8
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241773B2

Reaction notes

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