Water → 5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

HRID 1428123Notes

Reaction equation

HRID 1428123 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([CH3:24])[C:14]([CH3:16])([CH3:15])[O:13][B:12]([C:17]2[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=2)[O:11]1.O>CN(C=O)C>[Br:1][C:21]1[CH:22]=[C:17]([B:12]2[O:11][C:10]([CH3:24])([CH3:9])[C:14]([CH3:15])([CH3:16])[O:13]2)[C:18]([NH2:23])=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 438110672-Aminopyridine-3-boronic acid, pinacol ester

Product 1

HCID 867000765-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (255 mg) was added to a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg) in DMF (6.8 ml) at room temperature, and the mixture was stirred for four hours. Water was added and the precipitated solid was collected by filtration to give 210 mg of the title compound.

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4657539fb2ef4a72a457d2c930710a26
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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