Acetone → [(5-Bromopyridin-2-yl)methyl](propan-2-yl)amine

HRID 1520482Notes

Reaction equation

HRID 1520482 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](NC)=[N:6][CH:7]=1.[CH3:10][C:11]([CH3:13])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:28](#[N:30])C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:28][NH:30][CH:11]([CH3:13])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 156456635-Bromo-N-methylpyridin-2-amine

Product 1

HCID 62959892[(5-Bromopyridin-2-yl)methyl](propan-2-yl)amine

Procedure

To a solution of (5-Bromo-pyridin-2-yl)-methylamine (0.350 g, 1.871 mmol) in dry acetonitrile (7.0 mL) is added acetone (119 mg, 2.05 mmol) at room temperature. After stirring for 1 hour at room temperature, sodium Triacetoxy borohydride (595 mg, 2.807 mmol) is added then stir at room temperature for 16 hours. The volatiles are removed under reduced pressure, diluted with saturated aqueous bicarbonate solution and ethyl acetate. The organic layer separated and aqueous layer is extracted with ethyl acetate. Combined organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and crude is purified by column chromatography eluting in 6% methanol in CH2Cl2 to afford the title compound (160 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 0.98 (d, J=6.24 Hz, 6H), 2.66-2.73 (m, 1H), 3.76 (s, 2H), 7.44 (d, J=8.36 Hz, 1H), 7.97-7.80 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 8.59 (d, J=2.32 Hz, 1H). LC-MS (m/z): [M+H]=230.9.

Workup

  1. stirringthen stir at room temperature for 16 hours
  2. customThe volatiles are removed under reduced pressure
  3. additiondiluted with saturated aqueous bicarbonate solution and ethyl acetate
  4. customThe organic layer separated
  5. extractionaqueous layer is extracted with ethyl acetate
  6. dry with materialCombined organic layer is dried over sodium sulphate, solvent
  7. customis evaporated in vacuo and crude
  8. customis purified by column chromatography
  9. washeluting in 6% methanol in CH2Cl2

Sources & evidence

ORD record
ord-84e315b8562f45e2898240c458b5be5c
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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