Tetrabutylammonium Fluoride → HCID 68780659, compound

HRID 1878451Notes

Reaction equation

HRID 1878451 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=4)=[CH:14][N:13]3[CH:33]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.ClCCl.O>[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][NH:20][CH:19]=4)=[CH:14][N:13]3[CH:33]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68778463HCID 68778463, compound

Product 1

HCID 68780659HCID 68780659, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 120 mg of N-phenyl-6-(1-triisopropylsilyl-1H-pyrrol-3-yl)imidazo[1,2-a]pyridine-2-carboxamide in 5 mL of tetrahydrofuran is treated with 262 μL of a molar solution of tetrabutylammonium fluoride in tetrahydrofuran, and stirred for 10 minutes at room temperature. It is then diluted with 15 mL of dichloromethane and 20 mL of water. The organic phase is dried and concentrated to dryness under reduced pressure. The residue is taken up in 2 mL of dichloromethane, and the solid filtered off is washed twice with 1 mL of dichloromethane and then twice with 1 mL of diisopropyl ether, triturated twice with 2 mL of water, filtered off by suction and washed again with 2 mL of dichloromethane and 2 mL of diisopropyl ether and then dried to give 40 mg of N-phenyl-6-(1H-pyrrol-3-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid

Workup

  1. customThe organic phase is dried
  2. concentrationconcentrated to dryness under reduced pressure
  3. filtrationthe solid filtered off
  4. washis washed twice with 1 mL of dichloromethane
  5. customtwice with 1 mL of diisopropyl ether, triturated twice with 2 mL of water
  6. filtrationfiltered off by suction
  7. washwashed again with 2 mL of dichloromethane and 2 mL of diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-178beee5195349bd85f44fecb5c863ab
Source dataset
uspto-grants-2012_11
Patent number
US08314109B2

Reaction notes

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