Tetrahydrofuran → HCID 18466618, compound

HRID 2229331Notes

Reaction equation

HRID 2229331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][C:15]2[C:16](Cl)=[N:17][C:18]([Cl:22])=[CH:19][C:20]=2[CH3:21])=[O:13])[C:5]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH:9]3[CH2:11][CH2:10]3)[C:16]3[N:17]=[C:18]([Cl:22])[CH:19]=[C:20]([CH3:21])[C:15]=3[NH:14][C:12](=[O:13])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18466610HCID 18466610, compound

Product 1

HCID 18466618HCID 18466618, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-bromo-2-(cyclopropylamino)-N-(2,6-dichloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (105 mg, 0.254 mmol) in pyridine (3.0 mL) was heated to 50° C. while a 1 M solution of NaHMDS in THF (0.53 mL, 0.53 mmol) was added. The resulting solution was stirred at 50° C. for 3 h. The reaction was quenched with aqueous saturated NH4Cl, diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified via flash chromatography (hexane:EtOAc, 7:3) to give the title compound (32 mg, 33% yield).

Workup

  1. additionwas added
  2. customThe reaction was quenched with aqueous saturated NH4Cl
  3. additiondiluted with water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified via flash chromatography (hexane:EtOAc, 7:3)

Sources & evidence

ORD record
ord-7ae15e5a6c0549a1989c3e53a748f19b
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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