Hexane → HCID 18326223, compound

HRID 1250495Notes

Reaction equation

HRID 1250495 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:3]=1.CCCCCC.[Li]CCCC.[CH:39]([N:42]=[C:43]=[O:44])([CH3:41])[CH3:40]>C(OCC)C>[CH:39]([NH:42][C:43]([C:2]1[CH:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:3]=1)=[O:44])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 8058HexaneHCID 61277Isopropyl isocyanateHCID 21249824HCID 21249824, compoundHCID 178418339Butyllithium

Product 1

HCID 18326223HCID 18326223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2.22 g (0.0051 mol) of 2-bromo-4-{methyl(phenylmethyl)amino}-6-{3-(trifluoromethyl)phenoxy} pyridine was suspended in about 30 ml of diethyl ether. While cooling the obtained suspension in a dry ice-acetone bath in an argon atmosphere, 3.4 ml of a 1.65M-hexane solution of BuLi (0.0051×1.1 mol) was added thereto, followed by stirring the suspension for about 10 minutes. After 0.86 g (0.0051×2.0 mol) of isopropyl isocyanate dissolved in about 10 ml of diethyl ether was added to the reaction solution, the obtained solution was removed from the bath and stirred at room temperature for about one hour. The reaction solution was mixed with about 10 ml of a 1N-hydrochloric acid aqueous solution, and then distributed in ethyl acetate-saturated sodium bicarbonate water, followed by washing with saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. additionwas added
  2. additionwas added to the reaction solution
  3. customthe obtained solution was removed from the bath
  4. stirringstirred at room temperature for about one hour
  5. additionThe reaction solution was mixed with about 10 ml of a 1N-hydrochloric acid aqueous solution
  6. washby washing with saturated brine
  7. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-feb5820944114736935a2c1ca76d1a49
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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