4-Fluorobenzaldehyde → 5-[(4-Fluorobenzyl)amino]-pyridin-2-yl methyl sulfide

HRID 1789658Notes

Reaction equation

HRID 1789658 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:18][S:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 102611796-(Methylsulfanyl)pyridin-3-amine

Product 1

HCID 220361775-[(4-Fluorobenzyl)amino]-pyridin-2-yl methyl sulfideYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 344 μL (3.20 mmol) of 4-fluorobenzaldehyde and 449 mg (3.20 mmol) of 5-amino-2-methylthio-pyridine dissolved in 8 mL dichloromethane was added 1.11 g (5.25 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 5 h, and partitioned between ethyl acetate and water, dried over MgSO4 and concentrated to obtain 320 mg of 5-[(4-fluorobenzyl)amino]-pyridin-2-yl methyl sulfide, pure by 1H NMR.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f199975ddd8f47c0ab9cb67abdf59a3f
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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