Triphenylphosphine → HCID 70663306, compound

HRID 878323Notes

Reaction equation

HRID 878323 reaction equation
FC1C(F)=CC([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15](CCS(C)(=O)=O)[C:16](=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=C(OC)C=1.[F:40][C:41]1[CH:46]=[C:45]([F:47])[C:44]([O:48][CH3:49])=[CH:43][C:42]=1B(O)O.[F-].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.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.[Pd].[Pd]>[F:40][C:41]1[CH:46]=[C:45]([F:47])[C:44]([O:48][CH3:49])=[CH:43][C:42]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][CH3:16]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 522689Potassium FluorideHCID 70663214HCID 70663214, compoundHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663306HCID 70663306, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (4-iodo-pyridin-3-yl)-methyl-amine (100 mg, 0.43 mmol, example 98, intermediate b) in THF (3 mL) and water (1.5 mL) were added 2,4-difluoro-5-methoxyphenyl-boronic acid (231 mg, 0.85 mmol) and potassium fluoride (50 mg, 0.85 mmol) and the reaction mixture was purged with argon for 15 min. Then Pd2(dba)3 (78 mg, 0.09 mmol) and triphenyl phosphine (22 mg, 0.09 mmol) were added to the reaction mixture and the reaction mixture was stirred at 120° C. for 45 min in a microwave oven. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography eluting with a gradient of n-hexane:EtOAc (80:20 to 50:50) to give the desired compound as a yellow liquid (75 mg, 70%). MS (ESI): m/z=251.4 [M+H]+.

Workup

  1. customthe reaction mixture was purged with argon for 15 min
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography
  4. washeluting with a gradient of n-hexane:EtOAc (80:20 to 50:50)

Sources & evidence

ORD record
ord-7145bc63587b45b584aabc7f9a935155
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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