tert-Butyl isocyanate → (5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

HRID 1848564

Reaction equation

HRID 1848564 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Li]CCCC.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 68468634(5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

2,5-Dibromo-4-methylpyridine (1.83 g, 7.29 mmol) was dissolved in toluene (100 mL), cooled to −78° C. and a solution of nBuLi (4.4 mL, 8.8 mmol, 2.0 M in pentane) was added dropwise and stirred at −78° C. for 2 h. A solution of tBuNCO (1.1 mL, 9.5 mmol) in toluene (3 mL) was added dropwise and stirred for 1 h at −78° C. then warmed to −10° C. and quenched by addition of NH4Cl (aq). After warming to r.t. the reaction was extracted with ether and the organics dried over Na2SO4 and concentrated. The product was used without further purification. MS [M+H]+: 271.0; tR=2.44 min. (method 1)

Workup

  1. stirringstirred for 1 h at −78° C.
  2. temperaturethen warmed to −10° C.
  3. customquenched by addition of NH4Cl (aq)
  4. temperatureAfter warming to r.t. the reaction
  5. extractionwas extracted with ether
  6. dry with materialthe organics dried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was used without further purification

Sources & evidence

ORD record
ord-a2a4e62c06ae4a3ab68047fc7d2d9ef3
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Linked notes

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