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Tetrahydrofuran → 6-chloro-N-cyclohexyl-2-[2-(4-fluorophenyl)ethoxy]nicotinamide

HRID 2424906
ノート
印刷プレビュー

反応式

HRID 2424906 の反応式
Cl[C:2]1[C:7]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=[C:4]([Cl:17])[N:3]=1.[F:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24][OH:25])=[CH:21][CH:20]=1.C1COCC1>O1CCOCC1>[Cl:17][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])=[C:2]([O:25][CH2:24][CH2:23][C:22]2[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=2)[N:3]=1
参加物反応条件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 8028TetrahydrofuranHCID 820684-Fluorophenethyl AlcoholHCID 527624932,6-dichloro-N-cyclohexylnicotinamide2 回

生成物 1

HCID 598306816-chloro-N-cyclohexyl-2-[2-(4-fluorophenyl)ethoxy]nicotinamide収率 40.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

2,6-dichloro-N-cyclohexylnicotinamide (Intermediate 1, 273 mg, 1 mmol) was stirred in 1,4-dioxane (4 ml). To this solution was added 4-fluorophenethyl alcohol (154 mg, 1.1 mmol) followed by bis-sodium hexamethyldisilylamide 1.0M in THF (1.1 ml, 1.1 mmol). The tube was sealed and subjected to microwave heating 150° C. (Biotage Initiator 300 W) for 2 hours. The solvent was evaporated and the residue was diluted with water (15 ml) and extracted with dichloromethane (2×20 ml). The combined extract was washed with brine (20 ml) dried over MgSO4, filtered and evaporated. The crude product was purified on SiO2 (40 g) eluting with ethyl acetate/isohexane 0-40% and gave 6-chloro-N-cyclohexyl-2-[2-(4-fluorophenyl)ethoxy]nicotinamide (153 mg, 40%) as a white solid

後処理

  1. customThe tube was sealed
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with water (15 ml)
  4. extractionextracted with dichloromethane (2×20 ml)
  5. extractionThe combined extract
  6. washwas washed with brine (20 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified on SiO2 (40 g)
  11. washeluting with ethyl acetate/isohexane 0-40%

出典と根拠

ORDレコード
ord-ef46e12fb5634b5387d541d04851c4e1
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07964618B2

反応ノート

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