Triphenylphosphine → HCID 22504957, compound

HRID 1813966Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([Cl:9])[CH:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15](B(O)O)[CH:16]=1.[F-].[Cs+].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>[Cl:9][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[N:5]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 4-amino-2,6-dichloropyridine (1.0 g, 6.1 mmol), 5-chloro-2-methoxy-phenylboronic acid (1.4 g, 7.3 mmol) and palladium acetate (137 mg, 0.61 mmol) in ethylene glycol dimethyl ether (50 ml), degassed with argon, was added a solution of cesium fluoride (3.8 g, 24.4 mmol) in water (10 ml) followed by triphenylphosphine (320 mg, 1.22 mmol). After stirring at 85° C. for 12 hours, the mixture was filtered through a pad of celite under suction. The filtrate was dried over sodium sulfate and purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4 followed by 2:5) to provide 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyridin-4-yl-amine (720 mg, 44% yield). 1H NMR (acetone-d6) δ 3.91 (s, 3H, CH3), 5.92 (s, 2H, NH2), 6.60 (d, 1H, J=1.8 Hz, Ar), 7.14 (d, 1H, J=8.8 Hz, Ar), 7.33 (d, 1H, J=1.9 Hz, Ar), 7.37 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.90 (d, 1H, J=2.8 Hz, Ar).

Workup

filtrationthe mixture was filtered through a pad of celite under suction
dry with materialThe filtrate was dried over sodium sulfate
custompurified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4 followed by 2:5)

Sources & evidence

ORD record: ord-8d316e58e41844abb294694e9d9a7fb3
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875781B2

Reaction notes

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