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Potassium sodium tartarate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-(1-hydroxy-1-methyl-ethyl)-N-methyl-5-trifluoromethyl-benzamide

HRID 878062
ノート
印刷プレビュー

反応式

HRID 878062 の反応式
COC(=O)C1C=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:6]([C:7]([N:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH3:10])=[O:8])[CH:5]=1.[CH3:32][Mg]Br.[C:35]([CH:38]([CH:40]([C:42]([O-])=O)O)[OH:39])([O-])=O.[K+].[Na+]>C1COCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[N:9]([CH3:10])[C:7](=[O:8])[C:6]1[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:42]=[C:40]([C:38]([OH:39])([CH3:35])[CH3:32])[CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9855836Potassium sodium tartarateHCID 70663193N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl esterHCID 178418573HCID 178418573、化合物

生成物 1

HCID 70663326N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-(1-hydroxy-1-methyl-ethyl)-N-methyl-5-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester (200 mg, 446 μM, example 75) in THF (3.3 mL) were added methyl magnesium bromide (1M solution in butyl ether, 1.6 mL, 1.56 mmol) within 2 min. The reaction was poured on EtOAc (20 mL) and aqueous sodium potassium tartrate solution (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (20 mL) and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (115 mg, 57%). MS (ESI): m/z=449.123 [M+H]+.

後処理

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (20 mL)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

出典と根拠

ORDレコード
ord-ac7b7b39acd9477db4e05fea79256d15
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987307B2

反応ノート

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