Ethyl chloroformate → Ethyl [2-(5'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethyl]carbamate

HRID 1019698Notes

Reaction equation

HRID 1019698 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N(CC)C(C)C)(C)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][NH:16][C:18](=[O:19])[O:20][CH2:21][CH3:22])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 625867352-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-yl)ethylamine

Product 1

HCID 86661342Ethyl [2-(5'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethyl]carbamate

Procedure

The process is performed according to the method described in Example 1 (step 1.5.). Starting with 4.52 g (15.90 mmol) of 2-(5′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-ethylamine, prepared in step 10.2., 1.89 g (17.49 mmol) of ethyl chloroformate, 5.13 g (39.76 mmol) of N,N-diisopropylethylamine and 0.19 g (1.59 mmol) of N,N-dimethylaminopyridine, and after purifying on a column of silica gel, eluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 3.87 g of expected product are obtained in the form of a powder.

Workup

  1. customprepared in step 10.2
  2. washeluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 3.87 g of expected product
  3. customare obtained in the form of a powder

Sources & evidence

ORD record
ord-872e33a00e3d42edae8fad4fbd9c548d
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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