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Sodium Carbonate → 4-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 451481
ノート
印刷プレビュー

反応式

HRID 451481 の反応式
Br[C:2]1[C:3]2[N:4]([N:9]=[C:10]([NH2:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.CC1(C)C(C)(C)OB([C:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[NH2:12][C:10]1[N:11]=[C:3]2[C:2]([C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)=[CH:7][C:6]([CH3:8])=[CH:5][N:4]2[N:9]=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 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 214643388-Bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

生成物 1

HCID 673361314-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 53485975
CID 53485975
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 8-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.14 g, 5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.39 g, 7.5 mmol), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (204 mg, 250 μmol) and an aqueous solution of Na2CO3 (2 N, 12.5 mL, 25 mmol) in dioxane (50 mL) was stirred at 110° C. over night. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, the solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography using EtOAc as eluent. The title compound was obtained after stirring with diethyl ether, filtration and drying as a light yellow crystalline solid (1.54 g, 93%).

後処理

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue purified by silica gel chromatography

出典と根拠

ORDレコード
ord-77f426a3870f43ada43768e0dde0d823
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486967B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート