Toluene → HCID 67000912, compound

HRID 269051Notes

Reaction equation

HRID 269051 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:18]=[CH:19][N:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O>[CH:21]1([C:2]2[C:3]3[N:4]([CH:18]=[CH:19][N:20]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[CH:7]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 67000913HCID 67000913, compound

Product 1

HCID 67000912HCID 67000912, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 75806TricyclohexylphosphineCatalystHCID 962WaterSolvent

Procedure

To a Schlenk flask was added 8-bromo-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine (example C.25 step 3) (3.026 g, 8.9 mmol), cyclopropyl boronic acid (103 mg, 13 mmol), tri(cyclohexyl)phosphine (101 mg, 4 mol %), potassium phosphate (6.53 g, 31 mmol), 50 mL of toluene and 2.5 mL of water. The reaction mixture was degassed under Ar for 5 min, then palladium acetate (41 mg, 2 mol %) was added and continued to bubble in Ar, then placed into a 100° C. oil bath for 23 h. The cooled reaction mixture was decanted and filtered through a pad of celite/Si Gel, washed aqueous material with EtOAc and combined organic layers were concentrated to give a green-colored mixture. This residue was purified by silica gel column chromatography with heptane/EtOAc followed by trituration with heptane and very little ether to give the title compound as a green solid (1.79 g, 67%). MS (ISP) 303.1 [(M+H)+].

Workup

  1. customThe reaction mixture was degassed under Ar for 5 min
  2. additionpalladium acetate (41 mg, 2 mol %) was added
  3. customto bubble in Ar
  4. customplaced into a 100° C.
  5. customfor 23 h
  6. customThe cooled reaction mixture
  7. customwas decanted
  8. filtrationfiltered through a pad of celite/Si Gel
  9. washwashed aqueous material with EtOAc
  10. concentrationwere concentrated
  11. customto give a green-colored mixture
  12. customThis residue was purified by silica gel column chromatography with heptane/EtOAc

Sources & evidence

ORD record
ord-bd077c64302e40a8b4bfdc98a29659c9
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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