Cesium carbonate → HCID 66690540, compound

HRID 592289Notes

Reaction equation

HRID 592289 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16](Cl)[N:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)[N:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 214303362-Chloro-6-[(phenylmethyl)amino]-4-pyridinecarboxylic acid

Product 1

HCID 66690540HCID 66690540, compoundYield 57.7%

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(benzylamino)-6-chloroisonicotinic acid (0.9 g, 3.43 mmol) in THF (8.57 mL) and water (8.57 mL) were added (4-methylphenyl)boronic acid (0.70 g, 5.14 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.14 g, 0.17 mmol) and cesium carbonate (3.35 g, 10.3 mmol). The mixture was purged with nitrogen and was heated to 120° C. in the microwave reactor for 7 min. The mixture was filtered with Celite and saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→80% dichloromethane/methanol) gave the title compound (0.63 g): LC-MS [M+1]=318.9.

Workup

  1. customThe mixture was purged with nitrogen
  2. filtrationThe mixture was filtered with Celite and saturated aqueous sodium bicarbonate
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate (3×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (100% dichloromethane→80% dichloromethane/methanol)

Sources & evidence

ORD record
ord-e7962eb0511942f88e8122b524a64420
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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