Water → HCID 22063605, compound

HRID 1828544Notes

Reaction equation

HRID 1828544 reaction equation
[F:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.C([Li])CCC.Br[CH2:23][C:24]1[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=1.O>O1CCCC1>[F:1][C:2]1[C:3]([CH2:16][CH2:23][C:24]2[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 22063597HCID 22063597, compoundHCID 22063657Carbamic acid, (5-fluoro-4-methyl-2-pyridinyl)-, 1,1-dimethylethyl ester2×HCID 178418339Butyllithium

Product 1

HCID 22063605HCID 22063605, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The tert-butyl N-(5-fluoro-4-methyl-2-pyridyl)carbamate (75.6 mg, 0.334 mmol) obtained in (F) was dissolved in tetrahydrofuran (2 ml) and added dropwise with n-butyl lithium (1.5 M solution in hexane, 0.468 ml, 0.702 mmol) at −78° C. under argon atmosphere. The reaction mixture was warmed to room temperature, stirred for 1 hour, cooled to −78° C. again, added dropwise with a solution of 2-(bromomethyl)-4-isopropyl-1,3-thiazole (84.6 mg, 0.384 mmol) in tetrahydrofuran (2 ml), and then warmed to room temperature. The reaction mixture was added with water and extracted twice with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=100:1) to obtain the title compound (40.0 mg, 33%).

Workup

  1. temperaturecooled to −78° C. again
  2. temperaturewarmed to room temperature
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=100:1)

Sources & evidence

ORD record
ord-41735ae2c2d849568b5c5c729ab920a5
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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