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

HRID 1946300ノート

反応式

HRID 1946300 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 595479962-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzeneHCID 178522346HCID 178522346、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6afad93988045a5910276dc4c3ca229
出典データセット
uspto-grants-2013_03
特許番号
US08399436B2

反応ノート

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