Nitrogen → HCID 9968712, compound

HRID 2183929Notes

Reaction equation

HRID 2183929 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[N:17][C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([Sn](CCCC)(CCCC)[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)CCC.N#N>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[N:17][C:12]3=[N:11][CH:10]=2)=[CH:3][C:2]=1[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 69708751HCID 69708751, compound

Product 1

HCID 9968712HCID 9968712, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-(3-bromo-4-fluorophenyl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (70 mg, 0.19 mmol) and 4-(tri-n-butylstannyl)pyridine (107 mg, 0.29 mmol) in N,N-dimethylacetamide (3 ml) was degassed with N2. Tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.026 mmol) and copper(I) iodide (15 mg, 0.079 mmol) was added and the mixture heated at 80° C. for 6 h. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane and water, separated and the aqueous re-extracted with dichloromethane. The combined organics were washed with brine, dried (MgSO4) and evaporated. The residue was purified using preparative thin-layer chromatography on silica gel, using 30% ethyl acetate/dichloromethane as the eluent, to give a yellow solid. Further purification using preparative thin-layer chromatography on silica gel, eluting with 2% methanol/dichloromethane, afforded 3-[4-fluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a cream solid: δH (360 MHz, DMSO) 7.52 (1H, d, J 7), 7.63 (1H, dd, J 10 and 8), 7.71-7.73 (2H, m), 7.90 (1H, ddd, J 9, 5 and 2), 8.04 (1H, dd, J 7 and 2), 8.33 (1H, s), 8.72 (2H, m), 9.37 (1H, d, J 7); m/z (ES+) 359 (M++H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. customseparated
  4. extractionthe aqueous re-extracted with dichloromethane
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified
  9. customto give a yellow solid
  10. customFurther purification
  11. washeluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-f385d41225584e46bb40527ef59d01e4
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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