Acetic Acid → 1-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine

HRID 711272Notes

Reaction equation

HRID 711272 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([CH:8]=O)=[N:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][NH2:22].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([CH2:8][NH:22][CH2:21][C:14]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=2[O:12][CH3:11])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 121098645-Bromo-3-methylpyridine-2-carbaldehyde

Product 1

HCID 672087031-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 5-bromo-3-methylpicolinaldehyde 81-1 (1.0 g, 5 mmol), (2,4-dimethoxyphenyl)methanamine 81-2 (0.83 g, 5 mmol), acetic acid (0.9 g, 15 mmol) in DMF (10 mL) was added Na(OAc)3BH (2.46 g, 15 mmol) at room temperature. The reaction was stirred at room temperature overnight. The reaction was diluted with ethyl acetate and washed with aqueous Na2CO3 and brine. The organic phase was dried to give crude 1-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine 81-3. MS m/z 351.2 (M+1).

Workup

  1. washwashed with aqueous Na2CO3 and brine
  2. customThe organic phase was dried

Sources & evidence

ORD record
ord-3109a55b95ef432090eff16c2dfc374f
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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