Tin tetrachloride → (5-Amino-3-bromo-pyridin-2-yl)-carbamic acid tert-butyl ester

HRID 1029088Notes

Reaction equation

HRID 1029088 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl>CCO>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([NH2:15])=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 69810195Tert-butyl 3-bromo-5-nitropyridin-2-ylcarbamate

Product 1

HCID 65711617(5-Amino-3-bromo-pyridin-2-yl)-carbamic acid tert-butyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(3-Bromo-5-nitro-pyridin2-yl)-carbamic acid tert-butyl ester (100 mg, 0.31 mmol) and tin chloride (298 mg, 1.57 mmol) were dissolved in EtOH (3 mL), and stirred for 2 h at 40° C. The reaction solution was quenched with 2M NaOH, diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated to provide (5-amino-3-bromo-pyridin-2-yl)-carbamic acid tert-butyl ester (85 mg, 94% yield) as a brown solid.

Workup

  1. customThe reaction solution was quenched with 2M NaOH
  2. additiondiluted with EtOAc
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with EtOAc
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fc4b3b2fa35c40368dc2314c1dd528f3
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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