Potassium Carbonate → N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3'-bipyridine]-6'-carboxamide

HRID 711250ノート

反応式

HRID 711250 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([F:24])[CH:19]=3)=[N:16][CH:17]=2)=[O:9])=[N:6][CH:7]=1.[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[F:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][NH:10][C:8]([C:5]3[N:6]=[CH:7][C:2]([N:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]4=[O:25])=[CH:3][CH:4]=3)=[O:9])=[CH:17][N:16]=2)[CH:23]=[CH:22][N:21]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 672086435-bromo-N-((2'-fluoro-2,4'-bipyridin-5-yl)methyl)picolinamideHCID 178516071HCID 178516071、化合物

生成物 1

HCID 56599025N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3'-bipyridine]-6'-carboxamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

反応条件

温度
108 °C

実験手順

A mixture of 5-bromo-N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)picolinamide 38-4 (38.6 mg, 0.1 mmol), 2-hydroxypyridine 44-1 (19.0 mg, 0.2 mmol), CuI (9.5 mg, 0.05 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (7.1 mg, 0.05 mmol) and K2CO3 (28 mg, 0.20 mmol) in toluene (0.6 mL) was stirred at 108° C. for 8 hours. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was concentrated with rotavap. The residue was subjected to preparative reverse phase HPLC separation to give N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3′-bipyridine]-6′-carboxamide 44 as a solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite (washed with ethyl acetate)
  3. concentrationthe filtrate was concentrated with rotavap
  4. customThe residue was subjected to preparative reverse phase HPLC separation

出典と根拠

ORDレコード
ord-4175095b8e60402083459e4fcc7226c9
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

反応ノート

読み込み中…