5-Bromo-1-methyl-1H-imidazole → (1-Methyl-1H-imidazol-5-yl)(thiazol-5-yl)methanone

HRID 928738

반응식

HRID 928738 반응식
Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][CH:3]=1.C([Mg]Br)C.CON(C)[C:15]([C:17]1[S:21][CH:20]=[N:19][CH:18]=1)=[O:16]>C(Cl)Cl>[CH3:7][N:6]1[C:2]([C:15]([C:17]2[S:21][CH:20]=[N:19][CH:18]=2)=[O:16])=[CH:3][N:4]=[CH:5]1

참가 물질

5

반응물 3

HCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 25307138N-Methoxy-N-methyl-1,3-thiazole-5-carboxamideHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 86715592(1-Methyl-1H-imidazol-5-yl)(thiazol-5-yl)methanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-bromo-1-methyl-1H-imidazole (1.14 g, 7.11 mmol) in DCM was added ethyl magnesium bromide (2.34 mL, 7.11 mmol; 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting pale yellow solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0° C. and N-methoxy-N-methylthiazole-5-carboxamide (1.02 g, 5.92 mmol, Intermediate 11: step a) dissolved in DCM (3 mL) was added dropwise. The cold bath was removed and the reaction mixture stirred at room temperature for 48 hours. To the resulting yellow suspension was added water followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

후처리

  1. temperaturecooled in an ice bath to 0° C.
  2. additionwas added dropwise
  3. customThe cold bath was removed
  4. stirringthe reaction mixture stirred at room temperature for 48 hours
  5. additionTo the resulting yellow suspension was added water
  6. extractionThe aqueous mixture was extracted with DCM
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionEt2O was added
  11. customthe mixture sonicated
  12. filtrationThe precipitate was collected by filtration
  13. customdried

출처 및 근거

ORD 기록
ord-605fe22491404975a4da403d95aa5b3f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290476B2

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