Nitrogen → HCID 25070329, compound

HRID 1927152Notes

Reaction equation

HRID 1927152 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]>[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

7

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 1

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)Catalyst

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-bromopicolinamide (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 toulene (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. additionThen toulene (15.0 ml) was added
  2. customN2 was bubbled through the mixture for 10 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. customevaporation of the solvent
  5. additiondiluted with CH2Cl2-MeOH (1:1, 25 mL)
  6. filtrationfiltered through a pad of Celite™
  7. concentrationThe mixture was concentrated
  8. additionthe residue was diluted with MeOH
  9. customThe solution was purified by HPLC, 20%-70% of B in 35 min
  10. concentrationThe collected fractions were concentrated
  11. additionby adding aq. NaHCO3
  12. filtrationFiltration
  13. washrinse with water

Sources & evidence

ORD record
ord-c6ec8520c42f48428af006c6f22dbd40
Source dataset
uspto-grants-2012_05
Patent number
US08183258B2

Reaction notes

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