1,3-Bis(diphenylphosphino)propane → HCID 11499796, compound

HRID 1437759Notes

Reaction equation

HRID 1437759 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[O:17][CH3:18].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].OP([O-])(O)=O.[K+]>C1(C)C=CC=CC=1.ClCCl.CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([NH:14][C:13]2[CH:15]=[CH:16][C:10]([F:9])=[C:11]([O:17][CH3:18])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

9

Reactant 5

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 516951Monobasic potassium phosphateHCID 15165112-Chloro-4-iodopyridineHCID 27745334-Fluoro-3-methoxyanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 11499796HCID 11499796, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-iodopyridine (340.4 mg, 1.42 mmol) was dissolved in anhydrous toluene (15 mL), after which 4-fluoro-3-methoxyaniline (241.4 mg, 1.7 mmol), tris(dibenzylidineacetone)dipalladium(0) (26.5 mg, 0.028 mmol), 1,3-bis(diphenylphosphino)propane (23 mg, 0.06 mmol), and sodium-tert-butoxide (191.9 mg, 2.0 mmol) were added to the solution. This reaction mixture was stirred at reflux for 12-18 hours, after which the reaction was diluted in dichloromethane and filtered through Celite™. The Celite™ was washed with dichloromethane, and the resulting solution was concentrated to afford the product. This solid was collected and dried for 12-18 hours under vacuum. Purification (Biotage Horizon HPFC chromatography system, SiO2, 90:9:1 dichloromethane:methanol:ammonium hydroxide) yielded a light brown solid (18, 169 mg, 47%); HPLC: Inertsil ODS-3V C18, 30:70[KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 5.2 min, 93.6% purity.

Workup

  1. temperatureat reflux for 12-18 hours
  2. filtrationfiltered through Celite™
  3. washThe Celite™ was washed with dichloromethane
  4. concentrationthe resulting solution was concentrated
  5. customto afford the product
  6. customThis solid was collected
  7. customdried for 12-18 hours under vacuum
  8. customPurification (Biotage Horizon HPFC chromatography system, SiO2, 90:9:1 dichloromethane:methanol:ammonium hydroxide)
  9. customyielded a light brown solid (18, 169 mg, 47%)

Sources & evidence

ORD record
ord-322370f9ca654ba080c7e0be81269b65
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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