Cesium carbonate → 2,6-difluoro-N-[1-({2-methyl-4-[(2-pyridinylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

HRID 1946390ノート

反応式

HRID 1946390 の反応式
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:20])[N:8]=1)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br.Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1>CS(C)=O>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:15][C:14]=2[CH3:20])[N:8]=1)=[O:5]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 595479572,6-Difluoro-N-{1-[(4-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide

生成物 1

HCID 595480092,6-difluoro-N-[1-({2-methyl-4-[(2-pyridinylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 2,6-difluoro-N-{1-[(4-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide (for a preparation see Example 48)(103 mg, 0.30 mmol) in dimethyl sulfoxide (1 ml) was added cesium carbonate (195 mg, 0.60 mmol) and then 2-(bromomethyl)pyridine hydrobromide (107 mg, 0.423 mmol, Aldrich). The resulting red solution was stirred at ambient temperature under nitrogen overnight. The mixture was filtered using a hydrophobic frit and the filtrate diluted with methanol (1 ml). The filtrate was purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as an orange gum (28.3 mg); LCMS: (System 4) MH+=435, tRET=2.27 min.

後処理

  1. filtrationThe mixture was filtered
  2. additionthe filtrate diluted with methanol (1 ml)
  3. customThe filtrate was purified by MDAP on Sunfire C18 column
  4. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-d5774108eab8414da932f49114114620
出典データセット
uspto-grants-2013_03
特許番号
US08399436B2

反応ノート

読み込み中…