Morpholine → 4-((Morpholino)methyl)phenylboronic acid pinacol ester

HRID 2427520Notes

Reaction equation

HRID 2427520 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][CH:4]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C1COCC1>[CH3:16][C:11]1([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13][B:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:4][CH:5]=2)[O:10]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterYield 109.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (200 mg, 0.673 mmol) was dissolved in THF (5 mL) and morpholine (0.088 mL, 1.01 mmol) was added. The mixture stirred overnight at room temperature and was then filtered and concentrated to afford the title compound (223 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 7.79 (d, 2H), 7.36 (d, 2H), 3.73 (t, 4H), 3.55 (s, 2H), 2.47 (t, 4H).

Workup

  1. filtrationwas then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6702efa6100a4a41a9055870b6914183
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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