Diisopropylamine → HCID 58707368, compound

HRID 450851

Reaction equation

HRID 450851 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([C:30](OCC)=[O:31])=[CH:27][C:26]=2[CH:35]=1>C1COCC1>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([C:30]([C:19]3[C:14]([F:13])=[N:15][CH:16]=[CH:17][CH:18]=3)=[O:31])=[CH:27][C:26]=2[CH:35]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 97462-FluoropyridineHCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 58707368HCID 58707368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C. a solution of n-BuLi (0.73 ml, 1.17 mmol) is added to diisopropylamine (0.18 ml, 1.3 mmol). The mixture is stirred for 30 minutes at the same temperature before the resulting solution is added dropwise to a solution 2-fluoropyridine (0.1 ml, 1.17 mmol) in THF (3 ml) at −78° C. After stirring for one hour ethyl 5-methoxy-benzofuran-2-carboxylate (0.25 g, 1.17 mmol) in THF (4 ml) is added and stirring is continued for 2 hours at the same temperature. The reaction mixture is allowed to reach room temperature before quenching with saturated aqueous ammonium chloride solution. The product is extracted with ethyl acetate. Chromatography on silicagel gives the title compound, m.p. 130-134° C.

Workup

  1. additionis added
  2. stirringstirring
  3. waitis continued for 2 hours at the same temperature
  4. customto reach room temperature
  5. custombefore quenching with saturated aqueous ammonium chloride solution
  6. extractionThe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-4f9700d19aa143c8b8ca4e8e7adabb95
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Linked notes

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