2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

HRID 711360Notes

Reaction equation

HRID 711360 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:5][N:4]=1>CO.[Ni]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 574164952-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To the solution of 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine (500 mg, 1.79 mmol) in MeOH (50 mL) was added Raney-Ni (50 mg). The reaction mixture was stirred at room temperature under H2 for 2 h. Then the solid was filtered off, and the solvent was removed to afford 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine in 89% yield (400 mg). m/z 251 (M+H)+.

Workup

  1. filtrationThen the solid was filtered off
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-9363ef285a9b4f0b9bb2b4ec188fe041
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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