4-Fluoroaniline → HCID 57489613, compound

HRID 2044059Notes

Reaction equation

HRID 2044059 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:11][C:9]1[C:8]([F:12])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([F:13])=[CH:15][CH:16]=2)[N:10]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 27336592,6-Dichloro-5-fluoronicotinic acidHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 57489613HCID 57489613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,6-dichloro-5-fluoronicotinic acid (500 mg, 2.381 mmol) and 4-fluoroaniline (265 mg, 2.381 mmol) in THF (30 mL) was treated with 1 M lithium bis(trimethylsilyl)amide in THF (7.14 mL, 7.14 mmol) slowly and stirred at rt. Solvent was removed on rotary evaporator. The residue acidified with 1 N HCl, extracted into ethyl acetate, and concentrated to give a dark solid. LCMS: (M+H)+=285.12.

Workup

  1. customSolvent was removed on rotary evaporator
  2. extractionextracted into ethyl acetate
  3. concentrationconcentrated
  4. customto give a dark solid

Sources & evidence

ORD record
ord-5d643039e8e64a67b39a22dac1bf50dc
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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