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Cesium carbonate → Methyl 3-[[6-(4-hydroxy-4-methyl-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate

HRID 1427123
ノート
印刷プレビュー

反応式

HRID 1427123 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[C:12]([CH3:22])=[C:13]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:14]([O:16][CH3:17])=[O:15])=[O:9])[C:5]([CH3:23])=[CH:4][CH:3]=1.[CH3:24][C:25]1([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:31][C:25]1([CH3:24])[CH2:30][CH2:29][N:28]([C:2]2[N:7]=[C:6]([C:8]([NH:10][C:11]3[C:12]([CH3:22])=[C:13]([CH:18]=[CH:19][C:20]=3[CH3:21])[C:14]([O:16][CH3:17])=[O:15])=[O:9])[C:5]([CH3:23])=[CH:4][CH:3]=2)[CH2:27][CH2:26]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 156491744-Methylpiperidin-4-olHCID 86707343Methyl 3-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-2,4-dimethyl-benzoate

生成物 1

HCID 86707354Methyl 3-[[6-(4-hydroxy-4-methyl-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate収率 69.3%

試薬・触媒・溶媒

2
HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of methyl 3-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-2,4-dimethyl-benzoate (315 mg, 946.55 μmoles), 4-methylpiperidin-4-ol (130 mg, 1.13 mmol) and Cs2CO3 (0.9 g, 2.76 mmol) in 1,4-dioxane (7 ml) is added Pd(OAc)2 (25 mg, 89.93 μmoles) followed by racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (56 mg, 89.93 μmoles). The reaction mixture is purged with nitrogen for 5 minutes and then heated to reflux. After 2 hours, the reaction is cooled to ambient temperature and diluted with ammonium chloride and extracted with EtOAc. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 0-100% ethyl acetate in hexane to afford the title compound as a brown solid (0.27 g, 69%). Mass spectrum (m/z): 412.2 (M+1).

後処理

  1. customThe reaction mixture is purged with nitrogen for 5 minutes
  2. temperatureheated to reflux
  3. additiondiluted with ammonium chloride
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography (silica gel)

出典と根拠

ORDレコード
ord-534d0f8d9fea44018ae8e50d39cb248c
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933098B2

反応ノート

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