Sodium Carbonate → HCID 69421875, compound

HRID 1813975Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=1)=[O:5])[CH3:2].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH3:29])=[C:23](B(O)O)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([C:21]2[CH:20]=[C:19]([Cl:18])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-chloro-pyridine-2,6-dicarboxylic acid diethyl ester (700 mg, 2.8 mmol), 5-chloro-2-methoxy-phenylboronic acid (630 mg, 3.4 mmol), palladium acetate (105 mg, 0.47 mmol) in ethylene glycol dimethyl ether (50 ml), degassed with argon, was added a solution of sodium carbonate (868 mg, 8.2 mmol) in water (5 ml) followed by triphenylphosphine (220 mg, 0.84 mmol). The mixture was stirred at 80° C. for 3 hours and filtered through a pad of celite under suction. The filtrate was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2) to give 4-(5-chloro-2-methoxy-phenyl)-pyridine-2,6-dicarboxylic acid diethyl ester (755 mg, 74% yield) as a white solid. 1H NMR (acetone-d6) δ 1.42 (t, 6H, J=7.1 Hz CH3), 3.92 (s, 3H, CH3), 4.45 (q, 4H, J=7.1 Hz, CH2), 7.27 (d, 1H, J=8.9 Hz, Ar), 7.52 (dd, 1H J=8.8 Hz, J=2.7 Hz, Ar), 7.56 (d, 1H, J=2.7 Hz, Ar), 8.43 (s, 2H, Ar).

Workup

filtrationfiltered through a pad of celite under suction
customThe filtrate was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2)

Sources & evidence

ORD record: ord-2af62c54e9454834832af2f2f9aa7ce8
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875781B2

Reaction notes

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