Tetrahydrofuran → HCID 10427343, compound

HRID 583555Notes

Reaction equation

HRID 583555 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:13]([F:14])=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[F:15])[CH:2]=1.C(=O)(O)[O-].[Na+].C1COCC1.[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:34]([NH:11][C:10]1[CH:9]=[C:8]([F:15])[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:13]([F:14])[CH:12]=1)([O:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:35]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10242074HCID 10242074, compound

Product 1

HCID 10427343HCID 10427343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Pyridyl)-3,5-difluoroaniline (PREPARATION 2, 625 mg, 3.03 mmol), sodium bicarbonate (382 mg, 4.55 mmol, 1.5 eq) and dry THF (60 ml) are combined. The resulting mixture is placed under an atmosphere of nitrogen and benzylchloroformate (394 μl, 4.55 mmol, 1.5 eq) is added. The reaction is allowed to stir at 20-25°. After this time, the reaction is added to methylene chloride (150 ml) and washed with saturated sodium bicarbonate then brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to a solid which is puried by silica gel chromatography (200 g of silica gel, eluted with acetonitrile/chloroform (3/97-1 l, 5/95-21 l), the title compound is recovered as a solid, mp 188-190°; FTIR (neat) cm-1 3030, 1737, 1642, 1478, 1408, 1231, 1029, 723; MS (EI, m/z) 340, 296, 232, 205, 91, 79; NMR (CD3CL3) δ 8.59, 8.53-8.51, 7.95-7.92, 7.56-7.51, 7.44×7.31, 7.28 and 5.21.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialbrine, dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a solid which
  5. washeluted with acetonitrile/chloroform (3/97-1 l, 5/95-21 l)
  6. customthe title compound is recovered as a solid, mp 188-190°

Sources & evidence

ORD record
ord-9921b1709aea4476acdd675713c258d5
Source dataset
uspto-grants-1999_07
Patent number
US05929248

Reaction notes

Loading…