Sodium Hydroxide → N-(2,4-dimethoxybenzyl)-5-fluoropyridin-2-amine

HRID 1619707Notes

Reaction equation

HRID 1619707 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH:13]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 691752,4-DimethoxybenzaldehydeHCID 27377012-Amino-5-fluoropyridineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58042270N-(2,4-dimethoxybenzyl)-5-fluoropyridin-2-amineYield 112.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Fluoropyridin-2-amine (500 mg, 4.46 mmol) and 2,4-dimethoxybenzaldehyde (674 mg, 4.06 mmol) were stirred in dichloromethane (10 mL) at room temperature for 30 minutes. Sodium triacetoxyborohydride (1.3 g, 6.08 mmol) was added portion wise. The mixture was then stirred at room temperature for 18 hours before treatment with 1M aqueous sodium hydroxide solution (10 mL). The aqueous layer was separated and extracted with dichloromethane (10 mL). The combined organic layers were dried through a phase separating cartridge and evaporated to afford the title compound (1.2 g) as a brown solid.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane (10 mL)
  3. customThe combined organic layers were dried through a phase
  4. customseparating cartridge
  5. customevaporated

Sources & evidence

ORD record
ord-b6dc19769e9e4bbb8ebdb6d2e5a9dc9e
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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