Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate → 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

HRID 423229Notes

Reaction equation

HRID 423229 reaction equation
C(OC(=O)[NH:10][C:11]1[C:12]([O:26][CH3:27])=[N:13][CH:14]=[C:15]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:16]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:27][O:26][C:12]1[C:11]([NH2:10])=[CH:16][C:15]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)=[CH:14][N:13]=1

Participants

4

Reactant 1

HCID 16062737Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate

Product 1

HCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineYield 97%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

[2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-carbamic acid benzyl ester (506 mg, 1.32 mmol) was dissolved in methanol (10 mL). Pd(OH)2 on carbon (51 mg, 10 mol %) was added and the reaction was degassed with nitrogen. The nitrogen atmosphere was replaced by hydrogen and the reaction mixture was stirred at room temperature for 5 hours. The palladium residue was removed by filtration through a path of Celite, rinsing with more methanol. The filtrate was concentrated in vacuo to give the title compound as an off-white solid (319 mg, 97% yield). MS (ES+) m/e=251. 1H NMR (DMSO-d6) δH 1.27 (12H, s), 3.88 (3H, s), 4.89 (2H, br s), 7.13 (1H, s), 7.64 (1H, s).

Workup

  1. customthe reaction was degassed with nitrogen
  2. customThe palladium residue was removed by filtration through a path of Celite
  3. washrinsing with more methanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-352bdaa0f59143719c49046b6aa8a756
Source dataset
uspto-grants-2012_01
Patent number
US08101770B2

Reaction notes

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