Dimethylamine → 3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester

HRID 1157456Notes

Reaction equation

HRID 1157456 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:18][NH:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:18][N:19]([CH3:20])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[CH:4]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 27732832-[3-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 38036203-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol esterYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromomethylphenyl boronic acid pinacol ester (Combi Block Inc., 297 mg, 1.0 mmol) in acetonitrile (5 mL) was added dimethylamine (2M solution in methanol, 2.0 mmol) followed by the addition of K2CO3 (691 mg, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 h. Acetonitrile was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO3, dried (MgSO4), filtered and the filtrate concentrated in vacuo to give dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine (INTERMEDIATE XI.1) as a viscous oil (200 mg, 0.77 mmol, 77%).

Workup

  1. customAcetonitrile was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-9465784a057747d3a5cf1a1bb525b2c9
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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