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Potassium Carbonate → 4-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

HRID 516630
ノート
印刷プレビュー

反応式

HRID 516630 の反応式
C([O-])(O)=O.[Na+].[CH:6]1(B(O)O)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1I)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1[CH:6]1[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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

6

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 594971024-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one

生成物 1

HCID 594971164-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

試薬・触媒・溶媒 1

HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
175 °C

実験手順

NaHCO3 (1.0 g, excess), cyclopropylboronic acid (0.74 g, 8.93 mmol), potassium carbonate (1.23 g, 8.93 mmol) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II)-DCM complex (0.36 g, 0.45 mmol) were added to a solution of intermediate D10 (1.0 g, 2.98 mmol) in 1,4-dioxane (10 ml). The resulting mixture was heated at 175° C. for 20 minutes under microwave irradiation, after which it was filtered through diatomaceous earth and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo yielding D34 (0.6 g, 69%).

後処理

  1. filtrationafter which it was filtered through diatomaceous earth
  2. customthe solvent was evaporated in vacuo
  3. customThe crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
  4. customThe desired fractions were collected
  5. customevaporated in vacuo
  6. customyielding D34 (0.6 g, 69%)

出典と根拠

ORDレコード
ord-845de4cedd0046eaa462aadd49d1e39e
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09114138B2

反応ノート

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