Nitrogen → HCID 25070329, compound

HRID 645934Notes

Reaction equation

HRID 645934 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=1.[Cl:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])[C:24]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:23]2.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.N#N>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])[C:24]([S:35]([NH:38][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=1)(=[O:36])=[O:37])=[CH:23]2

Participants

8

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 6932914-BromopicolinamideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 59264630HCID 59264630, compound

Product 1

HCID 25070329HCID 25070329, compound

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The flask was charged with tris(dibenzylideneacetone)dipalladium (0) chloroform adduct (53.2 mg, 51.4 μmol), cesium carbonate (402 mg, 1.23 mmol), 4-bromo-picolinamide (103.4 mg, 0.514 mmol), 8-chloro-2-(2-chlorophenyl)quinoline-3-sulfonamide (200 mg, 0.566 mmol), tBuXPhos (37.0 mg, 77.2 μmol) and filled with N2. Then toluene (15.0 ml) was added and N2 was bubbled through the mixture for 10 minutes. The mixture was heated at 100° C. for 16 hours. The mixture was cooled to room temperature, evaporation of the solvent, diluted with CH2Cl2-MeOH (1:1, 25 mL), filtered through a pad of Celite™. The mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 20%-70% of B in 35 min. The collected fractions were concentrated and neutralized by adding aq. NaHCO3 Filtration and rinse with water gave 4-(8-chloro-2-(2-chlorophenyl)quinoline-3-sulfonamido)picolinamide, 1H-NMR (MeOD) δ 9.33 (s, 1H), 8.21 (d, J=8.0 Hz, 1H), 8.09 (d, J=7.8 Hz, 1H), 7.74 (t, J=7.8 Hz, 1H), 7.61 (s, 1H), 7.36-7.50 (m, 6H), 7.08 (d, J=8.0 Hz, 1H). Mass Spectrum (ESI) m/e=472.9 (M+1).

Workup

  1. customN2 was bubbled through the mixture for 10 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. customevaporation of the solvent
  4. additiondiluted with CH2Cl2-MeOH (1:1, 25 mL)
  5. filtrationfiltered through a pad of Celite™
  6. concentrationThe mixture was concentrated
  7. additionthe residue was diluted with MeOH
  8. customThe solution was purified by HPLC, 20%-70% of B in 35 min
  9. concentrationThe collected fractions were concentrated
  10. additionby adding aq.
  11. filtrationNaHCO3 Filtration
  12. washrinse with water

Sources & evidence

ORD record
ord-d952b757f376427080653a099f8c0321
Source dataset
uspto-grants-2010_04
Patent number
US07705018B2

Reaction notes

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