Potassium Carbonate → N-[1-({2-Chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

HRID 1946300노트

반응식

HRID 1946300 반응식
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[C:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:39]>CN(C=O)C>[Cl:39][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:25]=1[CH2:24][N:9]1[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:2]=2[F:1])=[N:8]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 595479962-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzeneHCID 178522346HCID 178522346, 화합물

생성물 1

HCID 59547897N-[1-({2-Chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 2,6-difluoro-N-(1H-pyrazol-3-yl)benzamide (for a preparation see Intermediate 9) (0.360 g, 1.61 mmol) and potassium carbonate (0.308 g, 2.23 mmol) was added a solution 2-(bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzene (for a preparation see Intermediate 8)(0.50 g, 1.61 mmol) in DMF (5 ml). The suspension was stirred overnight at ambient temperature. The suspension was partitioned between ethyl acetate (30 ml) and water (30 ml). The phases were separated and the organic phase washed with ethyl acetate (30 ml). The combined organic extracts were washed with brine (30 ml) and the solvent removed in vacuo. The residue was loaded in dichloromethane and purified on silica 50 g using 0-50% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (0.212 g); LCMS: (System 1) MH+=455, tRET=3.59 min.

후처리

  1. customThe suspension was partitioned between ethyl acetate (30 ml) and water (30 ml)
  2. customThe phases were separated
  3. washthe organic phase washed with ethyl acetate (30 ml)
  4. washThe combined organic extracts were washed with brine (30 ml)
  5. customthe solvent removed in vacuo
  6. custompurified on silica 50 g
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d6afad93988045a5910276dc4c3ca229
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

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