Methylamine → 1-(6-Bromopyridin-2-yl)-N-methylmethanamine

To a solution of 6-bromopyridine-2-carbaldehyde (1.00 g, 5.38 mmol) in CH2Cl2 (20 mL) was added methylamine (4.04 mL, 2M/THF, 8.08 mmol) then to the stirred solution was added sodium triacetoxyborohydride (1.37 g, 6.46 mmol). After stirring at rt for 18 h, the mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (100 mL). The layers were separated then the aqueous extracted with CH2Cl2 (2×30 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification via flash column chromatography (5% MeOH/CH2Cl2) afforded the desired compound: δH (CDCl3): 2.49 (3H, s), 3.86 (2H, s), 7.31 (1H, d), 7.38 (1H, d), 7.53 (1H, t).

1. customthe mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (100 mL)
2. customThe layers were separated
3. extractionthe aqueous extracted with CH2Cl2 (2×30 mL)
4. washThe combined organics were washed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification via flash column chromatography (5% MeOH/CH2Cl2)

ORD record

ord-60ef307150ea45d3adf1d6f2a047bacf

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173807B2