Ethyl Acetate → 6-Bromo-N-(4-fluorobenzyl)pyridin-2-amine

HRID 75925

Reaction equation

HRID 75925 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.CCOC(C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 96024-Fluorobenzyl chlorideHCID 3008092-Amino-6-bromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 639640646-Bromo-N-(4-fluorobenzyl)pyridin-2-amineYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 6-bromopyridin-2-amine (500 mg, 2.89 mmol), sodium tert-butoxide (695 mg, 7.24 mmol) in anhydrous toluene (20 ml) was added 4-fluorobenzylchloride (415 mg, 2.90 mmol) at room temperature. The reaction mixture was heated at 100° C. overnight. EtOAc was added and the mixture was washed with brine and was concentrated. Flash chromatography (10-14% EtOAc in hexanes) gave the title compound (506 mg, 63%). 1H NMR (CDCl3) δ 4.40 (m, 2H), 4.95 (br s, 1H), 6.20 (m, 1H), 6.73 (m, 1H), 7.00 (m, 2H), 7.25 (m, 3H).

Workup

  1. washthe mixture was washed with brine
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-412ecf97f443442880d9bf75aff4bf4f
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Linked notes

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