Sodium borohydride → 1-(6-Bromopyridin-3-yl)methanamine

HRID 2041481Notes

Reaction equation

HRID 2041481 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[N:9]O)=[CH:4][N:3]=1.[BH4-].[Na+]>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[NH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 76584761HCID 76584761, compound

Product 1

HCID 224505291-(6-Bromopyridin-3-yl)methanamineYield 73.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Add dropwise a solution of 2-bromo-pyridine-5-carbaldehyde oxime (0.5 g, 2.487 mmol) in DME (10 mL) to a solution of titanium(IV) chloride (0.573 mL, 5.223 mmol) and sodium borohydride (395 mg, 10.445 mmol) in DME (20 mL) at 0° C. Allow the mixture to warm to room temperature and stir for 3 h. Add water and remove the solvent in vacuo. Basify the mixture to pH 12 with 1N aqueous NaOH and extract with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to afford the desired intermediate (340 mg, 73%) that was used without further purification.

Workup

  1. customAdd water and remove the solvent in vacuo
  2. extractionBasify the mixture to pH 12 with 1N aqueous NaOH and extract with dichloromethane
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-735d9fb4afa14767ac88db9d11353f3c
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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