Di-tert-butyl dicarbonate → tert-Butyl (5,6-dichloropyridin-3-yl)carbamate

HRID 340264Notes

Reaction equation

HRID 340264 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[N:6][C:7]=1[Cl:8].[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:11](=[O:10])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 145952195-Amino-2,3-dichloropyridine

Product 1

HCID 22485189tert-Butyl (5,6-dichloropyridin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5,6-dichloropyridin-3-amine (commercially available) in THF (0.2 M) stirred at 0° C. was added (BOC)2O (1.2 eq). The reaction mixture was heated at 40° C. until full conversion as monitored by TLC. The reaction mixture was then concentrated. Flash chromatography (silica gel, 20-50% EtOAc in hexanes) of the elude afforded tert-butyl 5,6-dichloropyridin-3-ylcarbamate.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-e32e06252f044b25a719b8c8205d4830
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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