Hydrochloric Acid → 5-Chloro-4-(3-chlorophenyl)-pyridine-2-carboxylic acid

HRID 1480037

Reaction equation

[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:12])[CH:18]=2)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-chloro-4-iodo-pyridine-2-carboxylic acid (CAN 120643-06-3, 500 mg, 1.76 mmol) in toluene (10 mL) was added with stirring the [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium DCM complex (144 mg, 0.176 mmol), B-(3-chlorophenyl)-boronic acid (552 mg, 3.53 mmol) and sodium carbonate (467 mg, 4.41 mmol) in water (3 mL). The resulting mixture was stirred at 80° C. for 23 h, cooled, poured onto ice/water, acidified with hydrochloric acid (15 mL, 1 N) and partitioned between water and ethyl acetate. The organic portion was washed with brine, combined, dried over Na2SO4, filtered and concentrated. The crude product precipitated as brown solid from the concentrated solution and was used without further purification in the next step. MS (ESI, m/z): 268.1 (M).

Workup

temperaturecooled
additionpoured onto ice/water
custompartitioned between water and ethyl acetate
washThe organic portion was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product precipitated as brown solid from the concentrated solution
customwas used without further purification in the next step

Sources & evidence

ORD record: ord-2d70d6f69d29454781b85846bff6c1c6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Linked notes

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