Water → Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamate

HRID 1894814Notes

Reaction equation

HRID 1894814 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH2:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:25](OC([O-])=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH:15][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 22064466Tert-butyldicarbonateHCID 66591283[3-(5-Bromopyrid-2-yl)phenyl]methylamine

Product 1

HCID 86664991Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamateYield 81.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

1.07 g (4 mmol, 1 eq) of [3-(5-bromopyrid-2-yl)phenyl]methylamine are dissolved in 10 mL of dichloromethane in the presence of 1 mL of triethylamine and 200 mg of dimethylaminopyridine. 1.7 g (8 mmol, 2 eq) of tert-butyl dicarbonate are added and the reaction mixture is stirred overnight at 40° C. The reaction is stopped by adding 30 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.18 g of tert-butyl [3-(5-bromopyrid-2-yl)phenyl}methylcarbamate are obtained. Yield=81%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-0f1c5a6d494641f4b47e59853f2ace56
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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