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Methyl Acrylate → methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

HRID 887756
ノート
印刷プレビュー

反応式

HRID 887756 の反応式
Br[C:2]1[C:3]([C:23]([O:25][CH3:26])=[O:24])=[N:4][C:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:52]([O:56][CH3:57])(=[O:55])[CH:53]=[CH2:54]>CN(C)C=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:9]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[N:4]=[C:3]([C:23]([O:25][CH3:26])=[O:24])[C:2](/[CH:54]=[CH:53]/[C:52]([O:56][CH3:57])=[O:55])=[CH:7][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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

8

反応物 4

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 59145917Methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate

生成物 1

HCID 59145876methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate収率 81.3%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A suspension of methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate (3.16 g, 7.68 mmol), palladium acetate (172 mg, 0.768 mmol), triphenylphosphine (404 mg, 1.54 mmol), potassium carbonate-(1.59 g, 11.5 mmol) and methyl acrylate (1.21 mL, 15.4 mmol) in N,N-dimethylformamide (77 mL) was stirred with heating at 120° C. for 12 hr. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (2.60 g, yield 81%).

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

出典と根拠

ORDレコード
ord-aa8b62b95f7f40b28dabe8fd9b9a97e6
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247429B2

反応ノート

読み込み中…

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