Dimethylamine → [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]methanol

HRID 2427525Notes

Reaction equation

HRID 2427525 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:15]=[O:16])[CH:12]=[N:13][CH:14]=2)[O:3]1.CNC>>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:17])[O:3][B:4]([C:9]2[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=2)[O:5]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde

Product 1

HCID 46856339[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]methanolYield 80.3%

Procedure

10% Pd/c (100 mg) was flushed with argon in a flask, and ethanol was carefully added. 5(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-3-carbaldehyde (100 mg, 0.429 mmol) and dimethylamine (429 μL, 0.858 mmol) were added and the mixture stirred for 3 hrs under hydrogen. The reaction mixture was filtered through celite and the filterate was concentrated to afford an orang solid (81 mg, 80%). 1H NMR (300 MHz, CDCl3): δ 8.85 (d, 1H), 8.63 (d, 1H), 8.10 (d, 1M), 2.25 (s, 2H), 1.36 (s, 12H).

Workup

  1. custom10% Pd/c (100 mg) was flushed with argon in a flask
  2. additionethanol was carefully added
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filterate was concentrated

Sources & evidence

ORD record
ord-14987f3ada644356aec0e92533c98b9a
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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